HCID 70607488, compound → 1-(2-Methyl-3-sulfanylpropanoyl)-L-proline

HRID 262579Notes

Reaction equation

HRID 262579 reaction equation
C([O:5][C:6](=[O:37])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:36])[CH:13]([CH3:35])[CH2:14][S:15]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[SH:15][CH2:14][CH:13]([CH3:35])[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:37])=[O:5])=[O:36]

Participants

4

Reactant 1

HCID 70607488HCID 70607488, compound

Product 1

HCID 128775471-(2-Methyl-3-sulfanylpropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

1-[3-(triphenylmethylthio)-2-methylpropanoyl]-L-proline tert.butyl ester (5 g.) is dissolved in a mixture of anisole (55 ml.) and trifluoroacetic acid (110 ml.). After one hour storage at room temperature, the solvents are removed in vacuo and the residue is applied to a column of silica gel equilibrated with benzene:acetic acid (75:25) and eluted with the same solvent. The fractions corresponding to the component with Rf 0.40 (TLC silica gel with same system) are pooled and concentrated to dryness to yield 1-[3-mercapto-2-methylpropanoyl]-L-proline. Rf 0.62 (silica gel, chloroform/methanol:acetic acid:water 50:40:10), identical to the compound of Example 34.

Workup

  1. customthe solvents are removed in vacuo
  2. washeluted with the same solvent
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-caa219ffe95b4bceac4c5ae5dc7d6634
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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