Reacción #439562

ord-14c44ab99557493fb0719e65636b9976

Ecuación de reacción

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
Rendimiento 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
Rendimiento 95.3%

Reactantes

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

Reactivos

Ninguno

Disolventes

N
ammonia
CCO
ethanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe precipitate was collected by filtration
  2. 2
    Lavadowashed with a mixed solvent of water and ethanol (2:1)

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06747022B2uspto-grants-2004_06