Acetic Anhydride → HCID 15280843, compound

Participants

Reaction Steps

(1R,2S,3R,5R)-5-(4,5-Dichloro-2-nitroanilino)-3-(hydroxymethyl)-1,2-cyclopentanediol (1.30 g, 3.86 mmol) was stirred in pyridine (10 mL)-acetic anhydride (2.2 mL) at ambient temperature for 2 days. Volatiles were evaporated in vacuo and the residue partitioned between chloroform and saturated aqueous sodium bicarbonate. The chloroform layer was dried (sodium sulfate) and concentrated to an oil which was chromatographed on silica gel. Elution with 2% methanol-chloroform gave (1R,2S,3R,5R)-3-(acetoxymethyl)-5-(4,5-dichloro-2-nitroanilino)-1,2-cyclopentanediyl diacetate as yellow needles (1.60 g, 89%), after crystallization from ethyl acetate-hexanes, m.p. 125°-130° C.; 1H-NMR(DMSO-d6) and mass spectrum (CI) consistent with structure; [α]20589 -130.5°, [α]20578 -140°, [α]20546 -178° (c=0.275, methanol).

Provenance & Evidence