2,6-Dimethyl-benzoic acid 3-benzyloxycarbonylamino-4-tert-butoxycarbonyl-2-oxo-butyl ester → 2,6-Dimethyl-benzoic acid 3-amino-4-tert-butoxycarbonyl-2-oxo-butyl ester

HRID 722743Notes

Reaction equation

HRID 722743 reaction equation
C(OC([NH:11][CH:12]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13](=[O:26])[CH2:14][O:15][C:16](=[O:25])[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24])=O)C1C=CC=CC=1>CCO.Cl.[Pd]>[NH2:11][CH:12]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13](=[O:26])[CH2:14][O:15][C:16](=[O:25])[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24]

Participants

5

Reactant 1

HCID 235714152,6-Dimethyl-benzoic acid 3-benzyloxycarbonylamino-4-tert-butoxycarbonyl-2-oxo-butyl ester

Product 1

HCID 235714112,6-Dimethyl-benzoic acid 3-amino-4-tert-butoxycarbonyl-2-oxo-butyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2,6-Dimethyl-benzoic acid 3-benzyloxycarbonylamino-4-tert-butoxycarbonyl-2-oxo-butyl ester, 110, (11.3 g, 24.1 mmol) is dissolved in a solution of EtOH (400 mL) and 1N HCl (29 mL), treated with 10% Pd/C (500 mg) and stirred under a hydrogen atmosphere for 4 h. The solution is filtered and concentrated to yield 7.6 g of the desired product as an HCl salt that was used without further purification.

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-69f61c084564482fa02d80f8be138b78
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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