1-[1-(2-Toluoylmethyl)-2-oxo-5-benzyloxycarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea → 1-[1-(2-toluoylmethyl)-2-oxo-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

HRID 1979362Notes

Reaction equation

HRID 1979362 reaction equation
[C:1]1([CH3:48])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14](C(OCC3C=CC=CC=3)=O)[CH2:13][CH:12]([NH:32][C:33]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:37]=3)=[O:34])[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]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[NH:14][CH2:13][CH:12]([NH:32][C:33]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:37]=3)=[O:34])[C:11]2=[O:47])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 212015541-[1-(2-Toluoylmethyl)-2-oxo-5-benzyloxycarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

Product 1

HCID 212016301-[1-(2-toluoylmethyl)-2-oxo-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)ureaYield 63%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1-[1-(2-Toluoylmethyl)-2-oxo-5-benzyloxycarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea (1.00 g) obtained from Step 4 of Example 91 was dissolved in ethanol (20 ml), 10% palladium carbon (200 mg) was added, and under hydrogen atmosphere the mixture was stirred for 2 hours and addtionally stirred for one hour at 50° C. The reaction mixture was filtrated through a pad of Celite, the filtrate was concentrated under reduced pressure, to thereby obtain 500 mg of the titled compound.

Workup

  1. stirringaddtionally stirred for one hour at 50° C
  2. filtrationThe reaction mixture was filtrated through a pad of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-750a4d020e7d48a8b63bd4227c6676d2
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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