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

【结 构 式】

【分子编号】15828

【品名】(2R)-2-cyclopentyl-N-[(1S)-2-hydroxy-1-phenylethyl]-2-[4-(2-quinolinylmethoxy)phenyl]ethanamide

【CA登记号】

【 分 子 式 】C31H32N2O3

【 分 子 量 】480.60676

【元素组成】C 77.47% H 6.71% N 5.83% O 9.99%

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:(VII)

Separation of the Enantiomer: The enantiomers are separated from the racemic carboxylic acid (IV). After activation of the carboxylic acid group as imidazolide (V), this compound reacts with L-phenylglycinol and toluene sulfonic acid in DMF forming the diastereomeric mixture of L-phenylglycinolamides. These diastereomers can be separated by fractionated crystallization using ethanol (diastereomer VI) or a mixture of diethylether and isopropanol (diastereomer VII) as solvents. The release of enantiomerically pure carboxylic acids (VIII) and (IX) takes place by cleavage of the amide bond with sulfuric acid, neutralization and recrystallization from ethanol. The (R)-(-)-enantiomer is the active leukotriene synthesis inhibitor BAY X 1005.

1 Muller-Peddinghaus, R.; Raddatz, S.; BAY X 1005. Drugs Fut 1995, 20, 10, 996.
2 Mohrs, K.; Raddatz, S.; Perzborn, E.; Fruchtmann, R.; Kohlsdorfer, C.; Müller-Peddinghaus, R.; Theisen, P. (Bayer AG); Substd. 4-(quinoline-2-yl-methoxy)phenyl-acetic acid derivs. AU 8935270; DE 3900261; EP 0344519; JP 1990019359; JP 1998053577; US 4970215 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10973 (2S)-2-Amino-2-phenyl-1-ethanol; (S)-2-Hydroxy-1-phenylethylamine; (S)-(+)-2-Phenylglycinol; (S)-2-Amino-2-phenyl-1-ethanol 20989-17-7 C8H11NO 详情 详情
11353 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) 530-62-1 C7H6N4O 详情 详情
(IV) 15825 2-cyclopentyl-2-[4-(2-quinolinylmethoxy)phenyl]acetic acid C23H23NO3 详情 详情
(V) 15826 2-cyclopentyl-1-(1H-imidazol-1-yl)-2-[4-(2-quinolinylmethoxy)phenyl]-1-ethanone C26H25N3O2 详情 详情
(VI) 15827 (2S)-2-cyclopentyl-N-[(1S)-2-hydroxy-1-phenylethyl]-2-[4-(2-quinolinylmethoxy)phenyl]ethanamide C31H32N2O3 详情 详情
(VII) 15828 (2R)-2-cyclopentyl-N-[(1S)-2-hydroxy-1-phenylethyl]-2-[4-(2-quinolinylmethoxy)phenyl]ethanamide C31H32N2O3 详情 详情
(VIII) 15829 (2S)-2-cyclopentyl-2-[4-(2-quinolinylmethoxy)phenyl]ethanoic acid C23H23NO3 详情 详情
Extended Information