Acetic Acid → 1-[3-(Acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-L-proline

HRID 1762526Notes

Reaction equation

HRID 1762526 reaction equation
C([O:5][C:6](=[O:25])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:24])[CH:13]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:14][S:15][C:16](=[O:18])[CH3:17])(C)(C)C.C(O)(=O)C>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[C:16]([S:15][CH2:14][CH:13]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:25])=[O:5])=[O:24])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 545040181-[3-(acetylthio)-2-methoxycarbonylmethylpropanoyl]-L-proline tert-butyl ester

Product 1

HCID 541123831-[3-(Acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-L-proline

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

2.9 g. of the product from Example 80 is dissolved in a mixture of trifluoroacetic acid (17.5 ml.) and anisole (8.4 ml.). After one hour storage at room temperature, the excess trifluoraactic acid is removed in vacuo and the residue is precipitated twice from ether-hexane to yield 2.1 g. of the named product. Rf : 0.4 (silica gel-benzene:acetic acid, 75.25).

Workup

  1. customthe excess trifluoraactic acid is removed in vacuo
  2. customthe residue is precipitated twice from ether-hexane
  3. customto yield 2.1 g

Sources & evidence

ORD record
ord-1704886a3e394bb9acc1d1694ecd9e76
Source dataset
uspto-grants-1989_05
Patent number
US04833152

Reaction notes

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