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Volumn 39, Issue 30, 1998, Pages 5381-5384

Efficient hydrolysis of β-aminosulfamic acids using a lewis acid and a thiol for the synthesis of 2,3-diaminopropanoate derivatives

Author keywords

Amino acids and derivatives; Hydrolysis; Sulfamic acid and derivatives

Indexed keywords

2,3 DIAMINOPROPANOATE; BETA AMINOSULFAMIC ACID; DIETHYLAMINE; IMIDAZOLE DERIVATIVE; MORPHOLINE DERIVATIVE; PHENETHYLAMINE; PIPERIDINE DERIVATIVE; PROPIONIC ACID DERIVATIVE; PYRAZOLE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032560772     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01079-X     Document Type: Article
Times cited : (28)

References (27)
  • 3
    • 0028130028 scopus 로고
    • (c) Cole, D. C. Tetrahedron 1994, 50, 9517-9582;
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 5
    • 0025952925 scopus 로고
    • 2. For a review, see: (a) Huff, J. R. J. Med. Chem. 1991, 34, 2305-2314;
    • (1991) J. Med. Chem. , vol.34 , pp. 2305-2314
    • Huff, J.R.1
  • 13
    • 0028324801 scopus 로고
    • 4. See for example, Baldwin, J. E.; Adlington, R. M.; Mellor, L. C. Tetrahedron 1994, 50, 5049-66. Also see, Aguilera, B.; Fernandez-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-76.
    • (1994) Tetrahedron , vol.50 , pp. 5049-5066
    • Baldwin, J.E.1    Adlington, R.M.2    Mellor, L.C.3
  • 14
  • 15
    • 84944063670 scopus 로고    scopus 로고
    • 1,2-Oxa/thia-3-azoles
    • Kstritzky, A. R.; Rees, C. W.; Scriven, R. F. V. Eds.; Elsevier: Oxford
    • 5. For a review, see Khmelnitski, L. I.; Rakitin, O. A. 1,2-Oxa/thia-3-azoles. In Comprehensive Heterocyclic Chemistry II; Kstritzky, A. R.; Rees, C. W.; Scriven, R. F. V. Eds.; Elsevier: Oxford, 1996; pp. 409-432.
    • (1996) Comprehensive Heterocyclic Chemistry II , pp. 409-432
    • Khmelnitski, L.I.1    Rakitin, O.A.2
  • 19
    • 0026475477 scopus 로고
    • 9. Later it was established that the hydrolysis of the sulfamic acids occurred in the acidic reaction conditions (TFA/chloroform, reflux): Cooper, G. F.; McCathy, K. E.; Martin, M. M. Tetrahedron Lett. 1992, 33 , 5895-6.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5895-5896
    • Cooper, G.F.1    McCathy, K.E.2    Martin, M.M.3
  • 20
    • 0010421571 scopus 로고    scopus 로고
    • When the reaction was carried out with 1 equiv of piperidine and 4 equiv of diisopropylethylamine in the presence of a catalytic amount of TFA in refluxing chloroform, 15% of the desired diamine was obtained
    • 10. When the reaction was carried out with 1 equiv of piperidine and 4 equiv of diisopropylethylamine in the presence of a catalytic amount of TFA in refluxing chloroform, 15% of the desired diamine was obtained.
  • 22
    • 0028356205 scopus 로고
    • 12. For recent examples of acidic hydrolysis of sulfamic acids, see (a) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586;
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4585-4586
    • Okuda, M.1    Tomioka, K.2
  • 25
    • 0015915413 scopus 로고
    • 14. This is in fact closely related to similar A2 type hydrolysis of sulfate half esters reported by Kochansky and later by Sharpless, in which either a combination of a mineral or a Lewis acid along with a minimum amount of water can activate the sulfate half ester and assist the nucleophilic attack of nucleophiles (in these cases an ethereal solvent) onto the sulfur atom. See, (a) Goren, M. B.; Kochansky, M. E. J. Org. Chem. 1973, 38, 3510.
    • (1973) J. Org. Chem. , vol.38 , pp. 3510
    • Goren, M.B.1    Kochansky, M.E.2
  • 27
    • 0031464787 scopus 로고    scopus 로고
    • 15. Some α,β-diaminopropanoate structures are known to be labile to racemization. See for example: Yuan, C.; Williams, R. M. J. Am. Chem. Soc. 1997, 119, 11777-84.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11777-11784
    • Yuan, C.1    Williams, R.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.