2-(N-benzyloxycarbonyl-L-valyl)amino-6methylbenzoic acid → 6-methyl-2-(L-valylamino)benzoic acid

HRID 1729241Notes

Reaction equation

HRID 1729241 reaction equation
C(OC([NH:11][C@H:12]([C:16]([NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:20]=1[C:21]([OH:23])=[O:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1>CO.O.[Pd]>[CH3:28][C:24]1[C:20]([C:21]([OH:23])=[O:22])=[C:19]([NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH2:11])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 540687952-(N-benzyloxycarbonyl-L-valyl)amino-6methylbenzoic acid

Product 1

HCID 541805686-methyl-2-(L-valylamino)benzoic acidYield 105.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.21 g of 2-[(N-benzyloxycarbonyl-L-valyl)amino]-6-methylbenzoic acid was dissolved in a mixture of 99 ml of methanol and 1 ml of water, followed by adding 200 mg of 10% Pd-C. The mixture was stirred for 3 hours at room temperature under a hydrogen atmosphere. Pd-C was filtered off and the filtrate was concentrated to give 830 mg of 6-methyl-2-(L-valylamino)benzoic acid.

Workup

  1. filtrationPd-C was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-38e255c474b8422f802e2a9da34bdd50
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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