HCID 67490923, compound → HCID 67490825, compound

HRID 1917390Notes

Reaction equation

HRID 1917390 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:31][C:32]([OH:34])=[O:33])[C@@H:12]([CH2:13][O:14]CC2C=CC=CC=2)[C:11](=[O:22])[N:10]([C@@H:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[C].[Pd].CO>[C:1]([O:5][C:6]([C@@:8]1([CH2:31][C:32]([OH:34])=[O:33])[C@@H:12]([CH2:13][OH:14])[C:11](=[O:22])[N:10]([C@@H:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:24])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 67490923HCID 67490923, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67490825HCID 67490825, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A 10% palladium-carbon catalyst (3.93 g) was added to a solution of (3S,4S)-4-benzyloxymethyl-3-carboxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (3.93 g, 8.41 mmol) in methanol (84.0 mL) in a nitrogen atmosphere. After the atmosphere was replaced with hydrogen, the mixture was stirred in a hydrogen atmosphere at room temperature for three days. After the atmosphere was replaced with nitrogen, the reaction solution was filtered through Celite and concentrated under reduced pressure to give 2.54 g of the title compound.

Workup

  1. filtrationthe reaction solution was filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43090a3ea7c04ac5b37e4ac2b4978433
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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