4-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester → {1-[1-Cyclohexyl-2-oxo-2-(6-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl)-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 446979Notes

Reaction equation

HRID 446979 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]2[N:25]([C:28](=[O:50])[CH:29]([NH:36][C:37](=[O:49])[CH:38]([N:40]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH3:41])[CH3:39])[CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:26][CH2:27][CH:12]12)=O)C1C=CC=CC=1>CO.[Pd]>[C:45]([O:44][C:42](=[O:43])[N:40]([CH:38]([C:37](=[O:49])[NH:36][CH:29]([CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)[C:28](=[O:50])[N:25]1[CH2:26][CH2:27][CH:12]2[NH:11][CH2:15][CH:14]([C:16](=[O:24])[NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:13]12)[CH3:39])[CH3:41])([CH3:46])([CH3:47])[CH3:48]

Participants

4

Reactant 1

HCID 672822034-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-3-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Product 1

HCID 67280553{1-[1-Cyclohexyl-2-oxo-2-(6-phenylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl)-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 41 (440 mg, 0.64 mmol) and 10% palladium-on-carbon (88 mg) in MeOH (15 mL) was shaken at 48 psi under a H2 atmosphere. After 2 h, the mixture was filtered through a 0.45 μM filtering disc, washed with MeOH and concentrated to afford 42 (352 mg) as a white foam that was used without further purification. Mass spectrum, m/z [556.6] (M+H)+.

Workup

  1. filtrationthe mixture was filtered through a 0.45 μM
  2. filtrationfiltering disc
  3. washwashed with MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18f0994eaa2c43fabf05b5f5f7c74e64
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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