Trifluoromethanesulfonic acid → 1-[3-mercapto-2-(methylthio)propanoyl]-L-proline

HRID 262716Notes

Reaction equation

HRID 262716 reaction equation
C([O:5][C:6](=[O:28])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:27])[CH:13]([S:25][CH3:26])[CH2:14][S:15]CC1C=CC(OC)=CC=1)(C)(C)C.FC(F)(F)S(O)(=O)=O>ClCCl.C1(OC)C=CC=CC=1>[SH:15][CH2:14][CH:13]([S:25][CH3:26])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:28])=[O:5])=[O:27]

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 228056351-[3-(4-Methoxybenzylmercapto)-2-(methylthio)propanoyl]-L-proline tert-butyl ester

Product 1

HCID 228056361-[3-mercapto-2-(methylthio)propanoyl]-L-proline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

1-[3-(4-Methoxybenzylmercapto)-2-(methylthio)propanoyl]-L-proline tert-butyl ester (0.5 g.) is dissoled in a mixture of dichloromethane (2 ml.) and anisole (1.1 ml.) under a blanket of argon in an ice bath. Trifluoromethanesulfonic acid (1 g.) is added and the mixture is stirred at room temperature for thirty minutes. The solvent is removed in vacuo and the residue is distributed between water and ethyl acetate. The organic layer is washed six times with water, dried and concentrated to dryness in vacuo to yield 1-[3-mercapto-2-(methylthio)propanoyl]-L-proline.

Workup

  1. customThe solvent is removed in vacuo
  2. washThe organic layer is washed six times with water
  3. customdried
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-0128680f48354219a7e3a338a9c349c7
Source dataset
uspto-grants-1979_05
Patent number
US04154936

Reaction notes

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