4-(2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester → 4-(2-Amino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 1965189Notes

Reaction equation

HRID 1965189 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:10]2[N:22]([C:25](=[O:42])[CH:26]([NH:31]C(OCC3C=CC=CC=3)=O)[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:10]2[N:22]([C:25](=[O:42])[CH:26]([NH2:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 675174094-(2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 675062084-(2-Amino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl esterYield 104.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 46 (4.10 g, 7.02 mmol) and NH4OAc (275 mg, 3.50 mmol) in MeOH (70 mL) was treated with 10% Pd-on-carbon (wet, 745 mg, 0.70 mmol) and the stirred mixture was purged with hydrogen. After 3 h stirring under a balloon of hydrogen, TLC analysis (1:1 hexanes/EtOAc) indicated the reaction was complete. The catalyst was removed by filtration and the solvent was concentrated in vacuo. The residue was dissolved in Et2O and washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to provide 3.30 g of 47 as colorless oil which was used without further purification. Mass spectrum, m/z [449.9] (M+H)+.

Workup

  1. customthe stirred mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe solvent was concentrated in vacuo
  4. dissolutionThe residue was dissolved in Et2O
  5. washwashed successively with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1ed52ad641504e6ba4de35564c6b0bbd
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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