3-acetylthiopropanoyl-L-proline-t-butyl ester → 1-(3-Acetylthiopropanoyl)-L-proline

HRID 262550Notes

Reaction equation

HRID 262550 reaction equation
C([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:19])[CH2:13][CH2:14][S:15][C:16](=[O:18])[CH3:17])(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:16]([S:15][CH2:14][CH2:13][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:20])=[O:5])=[O:19])(=[O:18])[CH3:17]

Participants

4

Reactant 1

HCID 132082993-acetylthiopropanoyl-L-proline-t-butyl ester

Product 1

HCID 132083011-(3-Acetylthiopropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

1-(3-Acetylthiopropanoyl)-L-proline-t-butyl ester (4.7 g.) is dissolved in a mixture of anisole (34 ml.) and trifluoroacetic acid (68 ml.) and the mixture is kept at room temperature for one hour. The solvents are removed in vacuo and the residue is precipitated from ether-hexane several times. The residue (3.5 g.) is dissolved in acetonitrile (25 ml.) and dicyclohexylamine (2.8 ml.) is added. The crystalline salt is filtered and recrystallized from isopropanol. Yield 3.8 g.. m.p. 176°-177°. The salt is reconverted to 1-(3-acetylthiopropanoyl)-L-proline as in Example 1, yield 1.25 g., m.p. 89°-90° (ethyl acetate-hexane).

Workup

  1. customThe solvents are removed in vacuo
  2. customthe residue is precipitated from ether-hexane several times
  3. dissolutionThe residue (3.5 g.) is dissolved in acetonitrile (25 ml.)
  4. additiondicyclohexylamine (2.8 ml.) is added
  5. filtrationThe crystalline salt is filtered
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-72526ffb7fd945f8887c2fc703877777
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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