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【结 构 式】

【分子编号】55860

【品名】(2R)-2-[(methoxycarbonyl)amino]-3-phenylpropanoic acid

【CA登记号】

【 分 子 式 】C11H13NO4

【 分 子 量 】223.22856

【元素组成】C 59.19% H 5.87% N 6.27% O 28.67%

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:(II)

D-Phenylalanine (I) was protected as the methyl carbamate (II) by acylation with methyl chloroformate under Schotten-Baumann conditions. The N-methoxy amide (III) was then prepared by coupling of (II) with O-methyl hydroxylamine in the presence of EDC. Cyclization of (III) to the N-methoxy quinolinone (IV) was accomplished by treatment with bis(trifluoroacetoxy)iodobenzene in the presence of trifluoroacetic acid. Simultaneous reduction of the N-methoxy lactam and carbamate functions of (IV) by means of borane-methyl sulfide complex provided diamine (V). The aliphatic amino group of (V) was then selectively protected as the benzyl carbamate (VI) by using N-(benzyloxycarbonyloxy)succinimide at -40 C. Reaction of (VI) with phosgene, followed by treatment of the intermediate carbamoyl chloride with O-methyl hydroxylamine gave rise to the N-methoxy urea derivative (VII). This was cyclized with bis(trifluoroacetoxy)iodobenzene to the imidazoquinolinone (VIII). The N-methoxy and N-benzyloxycarbonyl groups of (VIII) were then removed by hydrogenolysis in the presence of Pearlman's catalyst, and the title compound was finally converted to the corresponding maleate salt.

1 Romero, A.G.; et al.; Synthesis of the selective D2 receptor agonist PNU-95666E from D-phenylalanine using a sequential oxidative cyclization strategy. J Org Chem 1997, 62, 19, 6582.
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) 11703 D-Phenylalanine; (R)-Phenylalanine 673-06-3 C9H11NO2 详情 详情
(II) 55860 (2R)-2-[(methoxycarbonyl)amino]-3-phenylpropanoic acid C11H13NO4 详情 详情
(III) 55861 methyl (1R)-1-benzyl-2-(methoxyamino)-2-oxoethylcarbamate C12H16N2O4 详情 详情
(IV) 55862 methyl (3R)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinylcarbamate C12H14N2O4 详情 详情
(V) 55863 N-methyl-N-[(3R)-1,2,3,4-tetrahydro-3-quinolinyl]amine; (3R)-N-methyl-1,2,3,4-tetrahydro-3-quinolinamine C10H14N2 详情 详情
(VI) 55864 benzyl methyl[(3R)-1,2,3,4-tetrahydro-3-quinolinyl]carbamate C18H20N2O2 详情 详情
(VII) 55865 benzyl (3R)-1-[(methoxyamino)carbonyl]-1,2,3,4-tetrahydro-3-quinolinyl(methyl)carbamate C20H23N3O4 详情 详情
(VIII) 55866 benzyl (5R)-1-methoxy-2-oxo-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-5-yl(methyl)carbamate C20H21N3O4 详情 详情
Extended Information