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【结 构 式】

【分子编号】64207

【品名】2-(2-methylphenyl)acetic acid

【CA登记号】

【 分 子 式 】C9H10O2

【 分 子 量 】150.1772

【元素组成】C 71.98% H 6.71% O 21.31%

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:(XIV)

The intermediate aldehyde (XXV) has been prepared by two related procedures. Benzylic bromination of o-tolylacetic acid (XIV) employing NBS and AIBN leads to bromo acid (XV), which is further converted into the tert-butyl ester (XVI) upon treatment with isobutylene and sulfuric acid. Bromide group displacement in (XVI) with NaN3 in hot DMF affords azide (XVII). This is then reduced by catalytic hydrogenation to the corresponding primary amine, which can be isolated as the more stable oxalate salt (XVIII). After protection of amine (XVIII) as the N-Boc derivative (XIX), selective reduction of the ester function employing LiAlH4 in cold Et2O gives rise to alcohol (XX). Further bromination of alcohol (XX) to produce (XXI) is accomplished by treatment with CBr4 and PPh3. Bromide (XXI) is condensed with 3-amino-1-propanol (XXII) yielding amino alcohol (XXIII), which is subsequently protected as the di-Boc derivative (XXIV). Swern oxidation of alcohol (XXIV) generates the required aldehyde intermediate (XXV).

1 Selnick, H.G.; Newton, R.C.; Newton, C.L.; Barrow, J.C.; Nantermet, P.G. (Merck & Co., Inc.); Thrombin inhibitors. WO 0311222 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIV) 64207 2-(2-methylphenyl)acetic acid C9H10O2 详情 详情
(XV) 64208 2-[2-(bromomethyl)phenyl]acetic acid C9H9BrO2 详情 详情
(XVI) 64209 tert-butyl 2-[2-(bromomethyl)phenyl]acetate C13H17BrO2 详情 详情
(XVII) 64210 tert-butyl 2-[2-(azidomethyl)phenyl]acetate C13H17N3O2 详情 详情
(XVIII) 64211 tert-butyl 2-[2-(aminomethyl)phenyl]acetate C13H19NO2 详情 详情
(XIX) 64212 tert-butyl 2-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acetate C18H27NO4 详情 详情
(XX) 64213 tert-butyl 2-(2-hydroxyethyl)benzylcarbamate C14H21NO3 详情 详情
(XXI) 64214 tert-butyl 2-(2-bromoethyl)benzylcarbamate C14H20BrNO2 详情 详情
(XXII) 18522 3-amino-1-propanol 156-87-6 C3H9NO 详情 详情
(XXIII) 64215 tert-butyl 2-{2-[(3-hydroxypropyl)amino]ethyl}benzylcarbamate C17H28N2O3 详情 详情
(XXIV) 64216 tert-butyl 2-{[(tert-butoxycarbonyl)amino]methyl}phenethyl(3-hydroxypropyl)carbamate C22H36N2O5 详情 详情
(XXV) 64217 tert-butyl 2-{[(tert-butoxycarbonyl)amino]methyl}phenethyl(3-oxopropyl)carbamate C22H34N2O5 详情 详情
Extended Information