反応 #439562

ord-14c44ab99557493fb0719e65636b9976

反応方程式

O
Water
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(=O)O)c2)CN(C2CCCCC2)c2ccccc21.O
(R)-(−)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid monohydrate
[Ca+2].[Cl-].[Cl-]
calcium chloride
→
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(=O)[O-])c2)CN(C2CCCCC2)c2ccccc21.CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(=O)[O-])c2)CN(C2CCCCC2)c2ccccc21.[Ca+2]
title compound
収率 95.3%
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(=O)[O-])c2)CN(C2CCCCC2)c2ccccc21.CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(=O)[O-])c2)CN(C2CCCCC2)c2ccccc21.[Ca+2]
calcium (R)-(−)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoate
収率 95.3%

反応物

O
Water
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(=O)O)c2)CN(C2CCCCC2)c2ccccc21.O
(R)-(−)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid monohydrate
—
aqueous solution
[Ca+2].[Cl-].[Cl-]
calcium chloride

試薬

なし

溶媒

N
ammonia
CCO
ethanol

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    ろ過The precipitate was collected by filtration
  2. 2
    洗浄washed with a mixed solvent of water and ethanol (2:1)

実験手順

In 220 ml of ethanol was suspended 22.0 g of (R)-(−)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid monohydrate. Under ice cooling, the resulting suspension was dissolved in 26.4 ml of concentrated aqueous ammonia. To the reaction mixture was added 22 ml of an aqueous solution of 3.05 g of calcium chloride, followed by stirring for 30 minutes. Water was added. The precipitate was collected by filtration and washed with a mixed solvent of water and ethanol (2:1), whereby 21.0 g of the title compound as powder was obtained.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06747022B2uspto-grants-2004_06