Water → Z 360

HRID 352380Notes

Reaction equation

HRID 352380 reaction equation
O.[C:2]([C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12][C@@H:11]([NH:26][C:27](=[O:38])[NH:28][C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32]([OH:34])=[O:33])[C:10]1=[O:39])=[O:7])([CH3:5])([CH3:4])[CH3:3].[Cl-].[Ca+2:41].[Cl-].O>C(O)C.N>[C:2]([C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12][C@@H:11]([NH:26][C:27](=[O:38])[NH:28][C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32]([O-:34])=[O:33])[C:10]1=[O:39])=[O:7])([CH3:5])([CH3:3])[CH3:4].[Ca+2:41].[C:2]([C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12][C@@H:11]([NH:26][C:27](=[O:38])[NH:28][C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32]([O-:34])=[O:33])[C:10]1=[O:39])=[O:7])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 67016731HCID 67016731, compound

Product 1

HCID 10170574Z 360Yield 95.3%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-14c44ab99557493fb0719e65636b9976
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

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