4-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester → 4-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

HRID 446961Notes

Reaction equation

HRID 446961 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH:7]2[CH2:20][CH2:21][N:22]([C:23](=[O:45])[CH:24]([NH:31][C:32](=[O:44])[CH:33]([N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH3:36])[CH3:34])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:6]12)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][NH:8][CH:7]2[CH2:20][CH2:21][N:22]([C:23](=[O:45])[CH:24]([NH:31][C:32](=[O:44])[CH:33]([N:35]([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[CH3:36])[CH3:34])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:6]12)=[O:4]

Participants

4

Reactant 1

HCID 672806884-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

Product 1

HCID 672826294-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl esterYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 18 (0.4 g, 0.64 mmol) in MeOH (20 mL) was treated with 10% Pd/C (wet, 216 mg) and reduced under an H2 atmosphere (50 psi) using a Parr apparatus. After 1.5 h, the mixture was filtered through a nylon filter cartridge and the solids were washed with MeOH. The filtrate was concentrated to afford 19 (0.31 g) as an orange-colored oil which was used without further purification. Mass spectrum, m/z [495.4] (M+H)+.

Workup

  1. filtrationthe mixture was filtered through a nylon
  2. filtrationfilter cartridge
  3. washthe solids were washed with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6d4ecdaee94542edb898458ebe0991e6
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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