Methyl (2S)-2-[(1S)-1-[(tert-butoxycarbonyl)amino]-2-oxo-2-pyrrolidin-1-ylethyl]pent-4-enoate → Methyl (2S)-2-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-oxo-2-pyrrolidin-1-ylethyl}pentanoate

HRID 2246240Notes

Reaction equation

HRID 2246240 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:17]([CH2:22][CH:23]=[CH2:24])[C:18]([O:20][CH3:21])=[O:19])[C:10](=[O:16])[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:17]([CH2:22][CH2:23][CH3:24])[C:18]([O:20][CH3:21])=[O:19])[C:10](=[O:16])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86617960Methyl (2S)-2-[(1S)-1-[(tert-butoxycarbonyl)amino]-2-oxo-2-pyrrolidin-1-ylethyl]pent-4-enoate

Product 1

HCID 86617961Methyl (2S)-2-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-oxo-2-pyrrolidin-1-ylethyl}pentanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product from Step B (1.54 g) in ethyl acetate (30 mL) was added 5% palladium on carbon (298 mg). The reaction mixture was stirred under hydrogen (1 atm) at room temperature for 2 h, then filtered through a pad of Celite and concentrated to give the desired product.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-edd19d686f30415ca77ec610ae431ebb
Source dataset
uspto-grants-2010_03
Patent number
US07687492B2

Reaction notes

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