Hydrochloric Acid → HCID 86739942, compound

Participants

Reaction Conditions

Reaction Steps

A solution of potassium carbonate (7.335 g, 53.08 mmole) in water (80 ml) was cooled to 0° C. and deoxygenated with argon. A solution of (±)-(cis)-[(3-azido-2-oxo-4-azetidinyl)methoxy]acetic acid, methyl ester (2.261 g, 10.62 mmole) in tetrahydrofuran (60 ml) was added and the mixture stirred at 0° C. for five minutes and then at room temperature for 5.5 hours. The reaction was cooled and acidified with 6N hydrochloric acid to pH 7. The tetrahydrofuran was mostly removed in vacuo, and the aqueous residue (pH ca. 8) was extracted with ethyl acetate. The aqueous layer was cooled to 0° C., acidified with 6N hydrochloric acid to pH 2, saturated with sodium chloride, and extracted with ethyl acetate (fifteen 80 ml portions). The organic extracts were dried (sodium sulfate), filtered, and concentrated in vacuo. The yield of crude acid was 1.503 g.

Provenance & Evidence