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【结 构 式】

【分子编号】51349

【品名】tert-butyl (4aS,5R)-2-cyclohexyl-1,3-dioxooctahydro-1H-pyrido[1,2-c]pyrimidin-5-ylcarbamate

【CA登记号】

【 分 子 式 】C19H31N3O4

【 分 子 量 】365.47296

【元素组成】C 62.44% H 8.55% N 11.5% O 17.51%

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:(IV)

The trans-3-amino-2-piperidineacetic acid derivative (I), obtained as a 5:1 mixture of (2S,3R)- and (2R,3S)-isomers, was condensed with cyclohexyl isocyanate (II) to produce urea (III). Base-catalyzed cyclization of (III) gave rise to the dioxo pyridopyrimidine (IV). Acid cleavage of the Boc group of (IV) afforded the corresponding mixture of enantiomeric trans-amines (V). Acylation of amines (V) with N-Boc-L-tryptophan (VI) by means of BOP as the coupling reagent furnished the corresponding mixture of diastereomeric amides from which the target isomer was isolated by preparative TLC.

1 Bartolomé-Nebreda, J.M.; et al.; 5-(Tryptophyl) amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-based potent and selective CCK1 receptor antagonists: Structure-activity relationship studies on the substituent at N2-position. J Med Chem 2001, 44, 13, 2219.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 44208 ethyl 2-[(2S,3R)-3-[(tert-butoxycarbonyl)amino]piperidinyl]acetate C14H26N2O4 详情 详情
(II) 18108 1-isocyanatocyclohexane; cyclohexyl isocyanate 3173-53-3 C7H11NO 详情 详情
(III) 51348 ethyl 2-[(2S,3R)-3-[(tert-butoxycarbonyl)amino]-1-[(cyclohexylamino)carbonyl]piperidinyl]acetate C21H37N3O5 详情 详情
(IV) 51349 tert-butyl (4aS,5R)-2-cyclohexyl-1,3-dioxooctahydro-1H-pyrido[1,2-c]pyrimidin-5-ylcarbamate C19H31N3O4 详情 详情
(V) 51350 (4aS,5R)-5-amino-2-cyclohexylhexahydro-1H-pyrido[1,2-c]pyrimidine-1,3(2H)-dione C14H23N3O2 详情 详情
(VI) 16114 N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid 13139-14-5 C16H20N2O4 详情 详情
Extended Information