• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】45392

【品名】N-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]acetamide

【CA登记号】130931-86-1

【 分 子 式 】C8H13NO2

【 分 子 量 】155.19676

【元素组成】C 61.91% H 8.44% N 9.03% O 20.62%

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:(V)

The hydrolysis of the chiral unsaturated bicyclic lactam (I) with aqueous refluxing HCl gives the amino acid (II), which is esterified with 2,2-dimethoxypropane, methanol and HCl to yield the methyl ester (III). The acylation of (III) with Ac2O and pyridine in dichloromethane affords the acetamide (IV), which is reduced with calcium borohydride in THF, providing the carbinol (V). The hydrolysis of the amido group of (V) with HCl in refluxing ethanol/water gives the chiral amino alcohol (VI), which is condensed with 2-amino-4,6-dichloropyrimidine (VII) by means of DIEA in refluxing butanol, yielding the adduct (VIII). The reaction of (VIII) with 4-chlorophenyldiazonium chloride (IX) by means of HOAc and NaOAc in water affords the azo compound (X), which is reduced with Zn and HOAc to provide the triaminopyrimidine (XI). The cyclization of (XI) with triethyl orthoformate gives the carbocyclic chloropurine (XII), which is finally treated with NaOH in refluxing water to yield the target carbocyclic guanine.

1 Evans, C.T.; et al.; Potential use of carbocyclic nucleosides for the treatment of AIDS - Chemo-enzymatic syntheses of the enantiomers of carbovir. J Chem Soc - Perkins Trans I 1992, 5, 589.
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) 33410 cis-2-azabicyclo[2.2.1]hept-5-en-3-one C6H7NO 详情 详情
(II) 33411 cis-4-amino-2-cyclopentene-1-carboxylic acid 168471-40-7 C6H9NO2 详情 详情
(III) 33412 methyl cis-4-amino-2-cyclopentene-1-carboxylate C7H11NO2 详情 详情
(IV) 45391 methyl (1S,4R)-4-(acetamido)-2-cyclopentene-1-carboxylate C9H13NO3 详情 详情
(V) 45392 N-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]acetamide 130931-86-1 C8H13NO2 详情 详情
(VI) 17647 [(1S,4R)-4-amino-2-cyclopenten-1-yl]methanol C6H11NO 详情 详情
(VII) 14404 4,6-dichloro-2-pyrimidinamine; 2-Amino-4,6-dichloropyrimidine; 4,6-dichloro-2-pyrimidinylamine 56-05-3 C4H3Cl2N3 详情 详情
(VIII) 17657 [(1S,4R)-4-[(2-amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H13ClN4O 详情 详情
(IX) 10197 4-Chlorobenzenediazonium chloride C6H4Cl2N2 详情 详情
(X) 17659 [(1S,4R)-4-([2-amino-6-chloro-5-[(E)-2-(4-chlorophenyl)diazenyl]-4-pyrimidinyl]amino)-2-cyclopenten-1-yl]methanol C16H16Cl2N6O 详情 详情
(XI) 17660 [(1S,4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H14ClN5O 详情 详情
(XII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
Extended Information