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【结 构 式】

【分子编号】54625

【品名】tert-butyl (1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethylcarbamate

【CA登记号】

【 分 子 式 】C16H24N2O2S

【 分 子 量 】308.44484

【元素组成】C 62.3% H 7.84% N 9.08% O 10.37% S 10.4%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XVII)

The reduction of N-Boc-L-phenylalanine (XIII) with B2H6 in THF gives the expected alcohol (XIV), which is oxidized with SO3/pyridine to yield the corresponding aldehyde (XV). The cyclization of (XV) with 2-sulfanylethylamine (XVI) affords the thiazolidine (XVII), which is dehydrogenated by means of MnO2 to afford the thiazole derivative (XVIII). Finally, the amino group of (XVIII) is deprotected with HCl to afford the desired intermediate, 2-phenyl-1(S)-(2-thiazolyl)ethylamine (XIX).

1 Tomioka, K.; et al.; An expeditious synthesis of dolastatin 10. Tetrahedron 1991, 32, 21, 2395.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(XIV) 54624 tert-butyl (1S)-1-benzyl-2-hydroxyethylcarbamate C14H21NO3 详情 详情
(XV) 23452 tert-butyl (1S)-1-benzyl-2-oxoethylcarbamate C14H19NO3 详情 详情
(XVI) 13186 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine 60-23-1 C2H7NS 详情 详情
(XVII) 54625 tert-butyl (1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethylcarbamate C16H24N2O2S 详情 详情
(XVIII) 54626 tert-butyl (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylcarbamate C16H20N2O2S 详情 详情
(XIX) 54607 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)-1-ethanamine; (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylamine C11H12N2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XX)

The reduction of N-Boc-L-phenylalanine (XVI) with diborane in THF gives N-Boc-L-phenylalaninol (XVII), which is oxidized with SO3/pyridine in DMSO to yield N-Boc-L-phenylalaninal (XVIII). The cyclization of (XVIII) with 2-sulfanylethylamine (XIX) affords the thiazolidine (XX), which is dehydrogenated by means of MnO2 to provide the thiazole derivative (XXI). Finally, compound (XXI) is N-deprotected by a treatment with TFA to provide the 2-phenyl-1(S)-(2-thiazolyl)ethylamine intermediate (XXII).

1 Pettit, G.R.; Srirangam, J.K.; Singh, S.B.; Williams, M.D.; Herald, D.L.; Barkóczy, J.; Kantoci, D.; Hogan, F.; Dolastatins 24. Synthesis of (-)-dolastatin 10. X-Ray molecular structure of N,N-dimethylvalyl-valyl-dolaisoleucine tert-butyl ester. J Chem Soc Perkins Trans I 1996, 8, Suppl. 3, 859-63.
2 Pettit, G.R.; Singh, S.B.; Williams, M.D.; Herald, D.L.; Hogan, F.; Burkett, D.D.; Clewlow, P.J.; The absolute configuration and synthesis of natural (-)-Dolastatin 10. J Am Chem Soc 1989, 111, Suppl. 3, 5463.
3 Pettit, G.R.; Singh, S.B. (Arizona State University); Synthesis of dolastatin 10. US 4978744 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVI) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(XVII) 54624 tert-butyl (1S)-1-benzyl-2-hydroxyethylcarbamate C14H21NO3 详情 详情
(XVIII) 23452 tert-butyl (1S)-1-benzyl-2-oxoethylcarbamate C14H19NO3 详情 详情
(XIX) 13186 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine 60-23-1 C2H7NS 详情 详情
(XX) 54625 tert-butyl (1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethylcarbamate C16H24N2O2S 详情 详情
(XXI) 54626 tert-butyl (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylcarbamate C16H20N2O2S 详情 详情
(XXII) 54607 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)-1-ethanamine; (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylamine C11H12N2S 详情 详情
Extended Information