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

HRID 903501Notes

Reaction equation

HRID 903501 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 dissolved 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-8c3dd7b5eba24cfc9bf5b399ef83b505
Source dataset
uspto-grants-1980_10
Patent number
US04228077

Reaction notes

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