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【结 构 式】

【分子编号】49084

【品名】N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)benzamide

【CA登记号】

【 分 子 式 】C17H16F3NO2

【 分 子 量 】323.3147896

【元素组成】C 63.15% H 4.99% F 17.63% N 4.33% O 9.9%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XVI)

Acylation of phenylalanine (XI) with benzoyl chloride (XII) under Schotten-Baumann conditions produced the corresponding benzamide (XIII). The cyclization of benzoylphenylalanine (XIII) in the presence of acetic anhydride afforded oxazolone (XIV), which was then reacted with trifluoroacetic anhydride producing the trifluoromethyl ketone (XV). After ketone (XV) reduction to carbinol (XVI) with NaBH4, the acidic hydrolysis of the benzamido group of (XVI) yielded the amino alcohol (XVII) (1). Condensation of acid (X) with amine (XVII) using EDC and HOBt gave amide (XVIII). The hydroxyl group of (XVIII) was then oxidized to ketone (XIX) employing a modified Pfitzner-Moffatt oxidation. Finally, hydrogenolysis of the benzyloxycarbonyl group of (XIX) furnished the desired aminopyrimidinone.

1 Akahoshi, F.; Ashimori, A.; Yoshimura, T.; et al.; Non-peptidic inhibitors of human chymase. Synthesis, structure-activity relationships, and pharmacokinetic profiles of a series of 5-amino-6-oxo-1,6-dihydropyrimidine-containing trifluoromethyl ketones. Bioorg Med Chem 2001, 9, 2, 301.
2 Akahoshi, F.; Yoshimura, T.; Eda, M.; Ashimori, A.; Fukuyama, H.; Nakajima, M.; Imada, T.; Okunishi, H.; Miyazaki, M. (Welfide Corporation); Heterocyclic amide cpds. and medicinal use of the same. EP 0826671; US 5948785; WO 9633974 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 49080 2-[5-[[(benzyloxy)carbonyl]amino]-2-(4-fluorophenyl)-6-oxo-1(6H)-pyrimidinyl]acetic acid C20H16FN3O5 详情 详情
(XI) 26219 Phenylalanine 150-30-1 C9H11NO2 详情 详情
(XII) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(XIII) 49081 N-Benzoyl-DL-phenylalanine 2901-76-0 C16H15NO3 详情 详情
(XIV) 49082 4-Benzyl-2-phenyl-2-oxazolin-5-one 5874-61-3 C16H13NO2 详情 详情
(XV) 49083 N-(1-benzyl-3,3,3-trifluoro-2-oxopropyl)benzamide C17H14F3NO2 详情 详情
(XVI) 49084 N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)benzamide C17H16F3NO2 详情 详情
(XVII) 49085 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol C10H12F3NO 详情 详情
(XVIII) 49086 benzyl 1-[2-[(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)amino]-2-oxoethyl]-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-5-pyrimidinylcarbamate C30H26F4N4O5 详情 详情
(XIX) 49087 benzyl 1-[2-[(1-benzyl-3,3,3-trifluoro-2-oxopropyl)amino]-2-oxoethyl]-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-5-pyrimidinylcarbamate C30H24F4N4O5 详情 详情
Extended Information