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

HRID 47130Notes

Reaction equation

HRID 47130 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-cc46fd5b198c48ac887ee9012fe6efa4
Source dataset
uspto-grants-1979_11
Patent number
US04176235

Reaction notes

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