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

HRID 2308800Notes

Reaction equation

HRID 2308800 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-adaaba07b33f4d71a383c33c39a82cbb
Source dataset
uspto-grants-1987_09
Patent number
US04690936

Reaction notes

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