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【结 构 式】

【分子编号】16604

【品名】1,3-thiazol-5-ylmethanol;5-thiazolylmethanol;Thiazole-5-methanol

【CA登记号】38585-74-9

【 分 子 式 】C4H5NOS

【 分 子 量 】115.15584

【元素组成】C 41.72% H 4.38% N 12.16% O 13.89% S 27.85%

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:(XX)

The thiazolyl carbonate (XI) has been synthesized as follows: The reaction of formamide (XIV) with P2S5 in ethyl ether gives thioformamide (XV), which is cyclized with 2-chloro-3-oxopropionic acid ethyl ester (XVI) [obtained by condensation of ethyl chloroacetate (XVII) with ethyl formate (XVIII) by means of t-BuOK in THF] yielding thiazol-5-carboxylic acid ethyl ester (XIX). The reduction of (XIX) with LiAlH4 in THF affords 5-thiazolylmethanol (XX), which is then esterified with 4-nitrophenyl chloroformate (XXI) by means of 4-methylmorpholine (MPH) in dichloromethane to give the desired product (XI).

1 Graul, A.; Castañer, J.; Ritonavir. Drugs Fut 1996, 21, 7, 700.
2 Kempf, D.J.; Norbeck, D.W.; Sham, H.L.; Zhao, C.; Sowin, T.J.; Reno, D.S.; Haight, A.R.; Cooper, A.J. (Abbott Laboratories Inc.); Retroviral protease inhibiting cpds. EP 0674513; EP 0727419; JP 1996505844; JP 1997118679; JP 1998087639; WO 9414436 .
3 Al-Razzak, L.; Marsh, K.C.; Manning, L.P.; Kaul, D. (Abbott Laboratories Inc.); Pharmaceutical compsns. containing HIV protease inhibitors. EP 0732923; US 5484801; WO 9520384 .
4 Flentge, C.; Kempf, D.; Marsh, K.; et al.; Symmetry-based inhibitors of HIV protease with high oral bioavailability. 207th ACS Natl Meet (March 13-17, San Diego) 1994, Abst MEDI 35.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 16595 4-nitrophenyl 1,3-thiazol-5-ylmethyl carbonate 144163-97-3 C11H8N2O5S 详情 详情
(XIV) 16598 Formamide 75-12-7 CH3NO 详情 详情
(XV) 16599 Thioformamide CH3NS 详情 详情
(XVI) 16600 ethyl 2-chloro-3-oxopropanoate C5H7ClO3 详情 详情
(XVII) 16601 ethyl chloroacetate; ethyl 2-chloroacetate 105-39-5 C4H7ClO2 详情 详情
(XVIII) 16602 ethyl formate 109-94-4 C3H6O2 详情 详情
(XIX) 16603 ethyl 1,3-thiazole-5-carboxylate 32955-22-9 C6H7NO2S 详情 详情
(XX) 16604 1,3-thiazol-5-ylmethanol;5-thiazolylmethanol;Thiazole-5-methanol 38585-74-9 C4H5NOS 详情 详情
(XXI) 16605 4-Nitrophenyl chloroformate; 1-[(Chlorocarbonyl)oxy]-4-nitrobenzene 7693-46-1 C7H4ClNO4 详情 详情

合成路线2

该中间体在本合成路线中的序号: (XXI)

中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
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