4-{2-[2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester → 4-[3-Methyl-2-(2-methylamino-propionylamino)-butyryl]-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 1965164Notes

Reaction equation

HRID 1965164 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]2[N:20]([C:23](=[O:45])[CH:24]([NH:28][C:29](=[O:44])[CH:30]([N:32](C(OCC3C=CC=CC=3)=O)[CH3:33])[CH3:31])[CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:22][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][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]2[N:20]([C:23](=[O:45])[CH:24]([NH:28][C:29](=[O:44])[CH:30]([NH:32][CH3:33])[CH3:31])[CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:22][CH:9]12)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 676088904-{2-[2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 676090284-[3-Methyl-2-(2-methylamino-propionylamino)-butyryl]-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl esterYield 51.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 mL Parr bottle was charged with crude 16 (50 mg, 0.08 mmol) and 10% Pd-on-carbon (50 mg) in reagent grade MeOH (3 mL). The mixture was pressurized to 50 PSI H2 then shaken for 2 h. The catalyst was removed by filtration through Celite® and the solids were washed with MeOH and EtOAc. The filtrate was concentrated in vacuo. The crude product was purified by RP-HPLC (2″ Dynamax® C18, 10-70% ACN/water containing 0.1% HOAc over 30 min; Flow: 40 mL/min) to afford 20 mg (51%) of 17 after lyophilization.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. washthe solids were washed with MeOH and EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe crude product was purified by RP-HPLC (2″ Dynamax® C18, 10-70% ACN/water containing 0.1% HOAc over 30 min

Sources & evidence

ORD record
ord-91c7199f51ee479d9f1bab358dd733de
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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