tert-butyl (1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethylcarbamate -Drug Synthesis Database

【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 合成路线2

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).

参考文献中间体

合成目标

【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).

参考文献中间体

合成目标

【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