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

HRID 569884Notes

Reaction equation

HRID 569884 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 trifluoroacetic 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 trifluoroacetic 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-73155958013d4483a2f6eecafc9a0de4
Source dataset
uspto-grants-1988_03
Patent number
US04734420

Reaction notes

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