(1-{1-[4-Benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester → HCID 67607310, compound

HRID 1965193Notes

Reaction equation

HRID 1965193 reaction equation
C(O[C:9](=O)[N:10]([CH:12]([C:14](=[O:50])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[N:28]([C:40](=[O:49])[NH:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:29][CH:30]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:24]12)=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])C)C1C=CC=CC=1>CO>[CH2:42]([NH:41][C:40]([N:28]1[CH2:29][CH:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH:24]2[N:23]([C:21](=[O:22])[CH:16]([NH:15][C:14](=[O:50])[CH:12]([NH:10][CH3:9])[CH3:13])[C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:27][CH2:26][CH:25]12)=[O:49])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

3

Reactant 1

HCID 67609238(1-{1-[4-Benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

Product 1

HCID 67607310HCID 67607310, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 50 (0.53 mmol) and NH4OAc (25 mg, 0.27 mmol) in MeOH (10 mL) was treated with 10% Pd-on-carbon (wet, 60 mg, 0.05 mmol) and the stirred mixture was purged with hydrogen. After 1 h stirring under a balloon of hydrogen, TLC analysis (10:1 DCM/MeOH) indicated the reaction was complete. The catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe filter and the solvent was removed in vacuo. The crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 10-60% ACN/water containing 0.1% HOAc over 25 min; Flow: 40 mL/min). Fractions containing pure product were combined, frozen, and lyophilized to provide 251 mg (84%, 2 steps) of 51 as a floculent white powder.

Workup

  1. customthe stirred mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe
  3. filtrationfilter
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 10-60% ACN/water containing 0.1% HOAc over 25 min
  6. additionFractions containing pure product
  7. temperaturefrozen

Sources & evidence

ORD record
ord-57da2e6ac2d04434b266463684d5878c
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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