Synthesis and derivatization of a versatile α-substituted lactam dipeptide isostere

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4319-4322

  Acton III, John J ^a   Jones, A Brian ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; DIPEPTIDE; GAMMA LACTAM DERIVATIVE; LACTAM;

ACYLATION; ALKYLATION; ARTICLE; DERIVATIZATION; DIASTEREOISOMER; ENANTIOMER; HYDROLYSIS; NUCLEAR OVERHAUSER EFFECT; PEPTIDE SYNTHESIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0029933030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00835-0     Document Type: Article

References (18)

1. This work will be described in future reports.
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8. It is, of course, important to correctly set the relative stereochemistry of the oxazolidinone product and to choose the correct configuration of amino acid, because the alkylation of the oxazolidinone will take place on the face opposite the 2-phenyl function. See ref. 7 ; also Seebach, D. and Fadel, A., Helv.Chim.Acta, 1985, 68, 1243; Fadel, A. and Salaün, J., Tetrahedron Lett., 1987, 28, 2243.
9. It is, of course, important to correctly set the relative stereochemistry of the oxazolidinone product and to choose the correct configuration of amino acid, because the alkylation of the oxazolidinone will take place on the face opposite the 2-phenyl function. See ref. 7 ; also Seebach, D. and Fadel, A., Helv.Chim.Acta, 1985, 68, 1243; Fadel, A. and Salaün, J., Tetrahedron Lett., 1987, 28, 2243.
10. As shown schematically below on the oxazolidinone made from L-methionine, irradiation of H-2 and H-4 indicate that the major isomer is the cis oxazolidinone. matrix presented
11. 2. Larger excesses of allyl iodide were avoided because of the possibility of S-alkylation.
12. 2 cyclization reaction did we observe the product as a single diastereomer. No ester hydrolysis was noted. Freidinger also reports an LDA mediated sulfonium salt cyclization to the lactam, while Thaisvirongs (ref. 5) uses lithium N-methylacetamide.
13. 3, 3H). MS: found: 388.1987; calculated 388.1998 [HRMS].
14. 3, 3H). MS: found: 256.1809; calculated 256.1787 [HRMS].
15. Brown, H.C., Knights, E.F., and Scouten, C.G., J. Am. Chem. Soc. 1974, 96, 7765.
16. Carlsen, P.H.J., Katsuki, T., Martin, V.S., and Sharpless, K.B., J. Org. Chem. 1981, 46, 3936.
17. Dodd, D.S. and Kozikowski, A.P., Tetrahedron Lett., 1994, 35, 977.
18. 3, 3H). MS: 648.6 (M+1) [ESI].