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

【结 构 式】

【分子编号】59019

【品名】methyl (3R)-3-amino-3-(4-hydroxyphenyl)propanoate

【CA登记号】

【 分 子 式 】C10H13NO3

【 分 子 量 】195.21816

【元素组成】C 61.53% H 6.71% N 7.17% O 24.59%

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 Michael addition of the chiral amine (II) to methyl 4-(benzyloxy)cinnamate (I) in the presence of butyllithium produces diastereoselectively the amino ester (III) as the major isomer. After catalytic hydrogenolysis of the benzyl groups of (III), the resultant amino ester (IV) is converted to the N-Boc derivative (V) upon treatment with Boc2O. O-alkylation of phenol (V) with iodomethane in the presence of Cs2CO3 yields methyl ether (VI). The N-Boc group of (VI) is subsequently removed under acidic conditions to furnish (VII).

1 Kopka, I.E.; Mumford, R.A.; Lin, L.S.; et al.; The discovery of acylated beta-amino acids as potent and orally bioavailable VLA-4 antagonists. Bioorg Med Chem Lett 2002, 12, 4, 611.
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) 59017 methyl (E)-3-[4-(benzyloxy)phenyl]-2-propenoate C17H16O3 详情 详情
(II) 47881 (1R)-N-benzyl-1-phenyl-1-ethanamine; N-benzyl-N-[(1R)-1-phenylethyl]amine C15H17N 详情 详情
(III) 59018 methyl (3R)-3-[4-(benzyloxy)phenyl]-3-{benzyl[(1R)-1-phenylethyl]amino}propanoate C32H33NO3 详情 详情
(IV) 59019 methyl (3R)-3-amino-3-(4-hydroxyphenyl)propanoate C10H13NO3 详情 详情
(V) 59020 methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate C15H21NO5 详情 详情
(VI) 59021 methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-(4-methoxyphenyl)propanoate C16H23NO5 详情 详情
(VII) 59022 methyl (3R)-3-amino-3-(4-methoxyphenyl)propanoate C11H15NO3 详情 详情
Extended Information