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【结 构 式】 
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【分子编号】51348 【品名】ethyl 2-[(2S,3R)-3-[(tert-butoxycarbonyl)amino]-1-[(cyclohexylamino)carbonyl]piperidinyl]acetate 【CA登记号】 |
【 分 子 式 】C21H37N3O5 【 分 子 量 】411.542 【元素组成】C 61.29% H 9.06% N 10.21% O 19.44% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |