Thionyl Chloride → 83552-28-7

Participants

Reaction Steps

To a stirred solution of (trans)-4- methylthio-L-proline, hydrochloride (1.5 g., 7.59 mmole) [Patchett et al., "Studies on Hydroxyproline", JACS, Vol. 79, p. 185-192 (1957)] in 40 ml. of methanol at -30° under argon is added 3.32 ml. (6 eq.) of thionyl chloride dropwise over 5 minutes. The reaction mixture is worked up according to the procedure of Example 95(e). Recrystallization from acetonitrile/ether gives 630 mg. of (trans)-4- (methylthio-L-proline, methyl ester, hydrochloride as a colorless, crystalline material; m.p. 155-156°; [α]D20 =-11.3° (c=1.71, methanol).

Provenance & Evidence