Hydrogen Bromide → HCID 178461467, compound

Participants

Reaction Steps

8.4 g. (0.024 mole) of (trans)-1-benzyloxycarbonyl-3-methylthio-D,L-proline are treated with 45 ml. of 4 N hydrobromic acid in acetic acid. After stirring for one hour at room temperature the solution is dried in vacuo. A small amount of water is added and this is washed twice with ether. The aqueous solution is applied to a column containing 300 ml. of an ion-exchange resin and water is passed through until the eluate is no longer strongly acidic. The product is then eluted with pH 6.5 (aqueous pyridine acetate) buffer. Fractions positive to ninhydrin are combined and lyophilized to give 3.4 g. (88%) of white fluff. A small sample of this material is crystallized from methanol to give (trans)-3-methylthio-D,L-proline; m.p. 196°-200° (dec.) (s. 192°).

Provenance & Evidence