Sodium → 1-(2-Methyl-3-sulfanylpropanoyl)-L-proline

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Reaction Steps

1-[3-(benzylthio)-2-methylpropanoyl]-L-proline (0.1 g.) is suspended in boiling liquid ammonia (10 ml.) and small pieces of sodium are added with stirring until persistent blue color. The color is discharged with a few crystals of ammonium sulfate and the ammonia is allowed to evaporate under a current of nitrogen. The residue is dissolved in a mixture of dilute hydrochloric acid and ethyl acetate. The organic layer is dried and concentrated to dryness in vacuo to yield 1-(3-mercapto-2-methylpropanoyl)-L-proline. Rf : 0.35 (Silica gel; Benzene/acetic acid 3:1), Rf 0.5 (Silica gel; Methyl-ethylketone/acetic acid/pyridine/water 14:1:2:1) identical to the compound of Example 34.

Provenance & Evidence