A convenient method for phosphorylation involving a facile oxidation of H-Phosphonate monoesters via bis(trimethylsilyl) phosphites

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7123-7126

  Wada, Takeshi ^a   Mochizuki, Akira ^a   Sato, Yuichi ^a   Sekine, Mitsuo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Nucleic acids; Oxaziridines; Oxidation; Phosphorylation

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; PHOSPHATE METABOLISM; PHOSPHORYLATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032563846     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01513-5     Document Type: Article

References (35)

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2. [2] Stawinski J. In: Engel R. editor. Handbook of organophosphorus chemistry. New York: Dekker, 1992:377-434.
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6. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
7. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
8. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
9. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
10. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
11. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
12. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
13. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
14. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
15. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
16. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
17. [4] Schefield JA, Todd AR. J. Chem. Soc. 1961:2316-2310. Hata T, Sekine, M. J. Am. Chem. Soc. 1974;96:7363-7364. Sekine M, Hata T. Tetrahedron Lett. 1975;1711-1714. Sekine M, Mori H, Hata T. Tetrahedron Lett. 1979:1145-1148. Garegg, PJ, Regberg T, Stawinski J, Strönberg R. Chemica Scripta 1986;26:59-62. Garegg, PJ, Lindh I, Regberg T, Stawinski J, Strönberg R. Tetrahedron Lett. 1986;27:4051-4054. Froehler BC, Ng PG, Matteucci MD. Nucleic Acids Res. 1986;14:5399-5407. Marugg JE, Tromp M, Kuyl-Yeheskiely E, van der Marel GA, van Boom JH. Tetrahedron Lett. 1986;27:2661-2664. Sekine M, Narui S, Hata T. Tetrahedron Lett. 1988;29:1037-1040. Takaku H, Yamakage S, Sakatsme O, Ohtsuki M. Chem Lett. 1988:1675-1678. Sakatsume O, Ohtsuki M, Takaku H, Reese CB. Nucleic Acids Res. 1989;17:3689-3697. Sakatsume O, Yamane H, Takaku H, Yamamoto N. Tetrahedron Lett. 1989;30:6375-6378. Stawinski J, Thelin M. Nucleosides Nucleotides 1990;9:120-135. Jankowska J, Sobkowski M, Stawinski J, Kraszewski A. Tetrahedron Lett. 1994;35:3355-3358. Kers A, Kers I, Stawinski J, Sobkowski M, Kraszewski A. Synthesis 1995:427-430. Bhongle NN, Tang JY. Tetrahedron Lett. 1995;36:6803-6806. Yang Z, Xu Z, Shen N, Fang Z. Nucleosides Nucleotides 1995;14:167-173. Ozola V, Reese CB, Song Q. Tetrahedron Lett. 1996;37:8621-8624.
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33. 3 (5 ml × 3). The aqueous layer was co-evaporated with EtOH and concentrated to dryness to give 3a (86 mg, 91%) as a colorless foam.
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