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【结 构 式】

【分子编号】27169

【品名】(2R)-3-cyclohexyl-2-methylpropionic acid

【CA登记号】

【 分 子 式 】C10H18O2

【 分 子 量 】170.25172

【元素组成】C 70.55% H 10.66% O 18.79%

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:(XXV)

The intermediate 3-cyclohexyl-2(R)-methylpropionyl chloride (XVIII) has been obtained as follows: The reaction of 4(S)-isopropyloxazolidin-2-one (XIX) with propionyl chloride (XX) by means of BuLi in THF gives 4(S)-isopropyl-3-propionyloxazolidin-2-one (XXI), which is condensed with benzyl bromide (XXII) by means of LHMDS in THF yielding 4(S)-isopropyl-3-(2(R)-methyl-3-phenylpropionyl)oxazolidin-2-one (XXIII). The oxidative cleavage of (XXIII) with H2O2 in THF/water affords 2(R)-methyl-3-phenylpropionic acid (XXIV), which is hydrogenated with H2 over alumina providing 3-cyclohexyl-2(R)-methylpropionic acid (XXV). Finally, this compound is treated with oxalyl chloride in DMF to afford the desired intermediate 3-cyclohexyl-2(R)-methylpropionyl chloride (XVIII).

1 Gauthier, J.-A.; Moss, N. (Bio-Mega, Inc.; Boehringer Ingelheim GmbH); Herpes ribonucleotide reductase inhibitors. EP 0837845; JP 1999508246; US 5672586; WO 9700855 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVIII) 27157 (2R)-3-cyclohexyl-2-methylpropanoyl chloride C10H17ClO 详情 详情
(XIX) 12867 (4S)-4-Isopropyl-1,3-oxazolidin-2-one; (R)-4-Isopropyl-2-oxazolidinone 17016-83-0 C6H11NO2 详情 详情
(XX) 15967 propanoyl chloride; propionyl chloride 79-03-8 C3H5ClO 详情 详情
(XXI) 11535 (4S)-4-Isopropyl-3-propionyl-1,3-oxazolidin-2-one 77877-19-1 C9H15NO3 详情 详情
(XXII) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(XXIII) 27167 (4S)-4-isopropyl-3-[(2R)-2-methyl-3-phenylpropanoyl]-1,3-oxazolidin-2-one C16H21NO3 详情 详情
(XXIV) 27168 (2R)-2-methyl-3-phenylpropionic acid C10H12O2 详情 详情
(XXV) 27169 (2R)-3-cyclohexyl-2-methylpropionic acid C10H18O2 详情 详情
Extended Information