Benzyl rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate → Rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamic acid

HRID 275597Notes

Reaction equation

HRID 275597 reaction equation
[C:1]([C:4]([S:7]([CH2:10][CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])(=[O:9])=[O:8])([CH3:6])[CH3:5])(=[O:3])[NH2:2]>CO.[Pd]>[C:1]([C:4]([S:7]([CH2:10][CH:11]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])([CH3:6])[CH3:5])(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 54066967Benzyl rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate

Product 1

HCID 54501271Rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamic acidYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 0.74 g (1.83 mmol) of benzyl rac-α-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate and 200 mg of palladium/charcoal (5%) in 30 ml of methanol was hydrogenated at room temperature under normal pressure for 2 hours. Subsequently, the catalyst was filtered off and the solution was evaporated under reduced pressure. There was obtained 0.54 g of rac-α-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamic acid as a colourless solid, MS: 314 (M+H)+.

Workup

  1. filtrationSubsequently, the catalyst was filtered off
  2. customthe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-beea76b7b7104c65b93b5f4c1d531502
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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