1-[2-Acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline → 1-(5-Amino-2-mercaptomethylpentanoyl)-L-proline

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Reaction Steps

1-[2-Acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline (1 g.) is dissolved in concentrated ammonia (20 ml.) under a blanket of argon and the solution is kept at room temperature for one hour. The excess ammonia is removed in vacuo and the residue is applied to a column of Dowex 50 in the hydrogen cycle. The column is washed with water and the 1-(5-amino-2-mercaptomethylpentanoyl)-L-proline is eluted with a 2 M buffer of pyridine-acetic acid at pH 6.5. Rf =0.5 [CHCl3, MeOH, 38% AcOH (3:2:1)].

Provenance & Evidence