tert-butyl (4aS,5R)-2-cyclohexyl-1,3-dioxooctahydro-1H-pyrido[1,2-c]pyrimidin-5-ylcarbamate -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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