Anisole → 1-(3-Acetylthiopropanoyl)-L-proline

HRID 2419418Notes

Reaction equation

HRID 2419418 reaction equation
C([O:5][C:6](=[O:19])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][CH2:13][CH2:14][S:15][C:16](=[O:18])[CH3:17])(C)(C)C.C1([O:26]C)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:5])=[O:19])=[O:26])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 228045971-(3-Acetylthiopropanyl)-L-proline-t-butyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(3-Acetylthiopropanyl)-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 1 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-6ee5871be6a4482d8cd4920d41ede9b0
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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