HCID 21201696, compound → HCID 21201788, compound

HRID 1979319Notes

Reaction equation

HRID 1979319 reaction equation
[C:1]1([CH3:48])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13][CH:12]([NH:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([O:39]CC4C=CC=CC=4)=[O:38])[CH:32]=3)=[O:29])[C:11]2=[O:47])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1>C(O)C.[C].[Pd]>[C:1]1([CH3:48])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([C:21](=[O:26])[C:22]([CH3:24])([CH3:25])[CH3:23])[CH2:13][CH:12]([NH:27][C:28](=[O:29])[NH:30][C:31]3[CH:32]=[C:33]([CH:34]=[CH:35][CH:36]=3)[C:37]([OH:39])=[O:38])[C:11]2=[O:47])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 21201696HCID 21201696, compound

Product 1

HCID 21201788HCID 21201788, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% Palladium carbon (200 mg) was added to a solution of 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-benzyloxycarbonylphenyl)urea (1.4 g) obtained from Step 3 in ethanol (50 ml), stirred for 8 hours at room temperature under hydrogen atmosphere. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure, to thereby obtain 1.04 g of (+)-3-[3-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acid (Yield: 86%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b8149ceb68941b0829edcd7ffbffefa
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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