benzyloxycarbonyl-L-valyl-L-proline t-butyl ester → tert-butyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylate

HRID 2293801Notes

Reaction equation

HRID 2293801 reaction equation
[C:1]([O:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:28])[C@H:13]([CH:25]([CH3:27])[CH3:26])[NH:14]C(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:28])[C@H:13]([CH:25]([CH3:26])[CH3:27])[NH2:14])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 10549214benzyloxycarbonyl-L-valyl-L-proline t-butyl ester

Product 1

HCID 11196516tert-butyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylateYield 103.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[(Phenylmethoxy)carbonyl]-L-valyl-L-proline tert-butyl ester (905 g) was dissolved in ethanol (4 litres) and 10% palladium on carbon (20 g) was added. The reaction mixture was shaken under a hydrogen atmosphere (50 psi) for 12 hours and then the catalyst was removed by filtration through diatomaceous earth. The filtrate was concentrated under vacuum and the residue twice re-evaporated from toluene (1 litre) to give L-Valyl-L-Proline tert-butyl ester as an oil (628 g); TLC, Rf =0.2, acetone:hexane (20:80); MS: m/z=271(M+1).

Workup

  1. customthe catalyst was removed by filtration through diatomaceous earth
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue twice re-evaporated from toluene (1 litre)

Sources & evidence

ORD record
ord-0adbd3be007f4164969b55bb757d43b0
Source dataset
uspto-grants-1997_11
Patent number
US05686628

Reaction notes

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