Citric Acid → HCID 86749456, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 15.0 g (62.2 mmol) of trans-4-allyloxycarbonylaminomethylcyclohexanecarboxylic acid in 550 mL of benzene and 9.1 mL (65.3 mmol) of triethylamine was heated to 45° C under Ar. Diphenylphosphoryl azide (14.1 mL, 65.3 mmol, Aldrich) was added in one portion, and the solution stirred for 24 h at 45° C. The solution was cooled to 10° C. and 65 mL of a 1.0M solution of lithium tbutoxide in THF (Aldrich) was added such that the reaction temperature remained between 8°-10° C. A second 65 mL portion of t-butoxide solution was added, and the solution stirred for 45° C at 8°-12° C. This solution was then poured into a rapidly stirred mixture of 1M aq. citric acid and ice, and the resulting mixture stirred for 1 h. This mixture was extracted with 2 portions of ethyl acetate, the combined organic layers washed with 2×10% Na2CO3, brine, and dried over Na2SO4. This solution was poured through a pad of 150 g of silica gel, and the pad washed with 2×300 mL of ethyl acetate. Evaporation of the filtrate gave 15.9 g (82%) of the title compound as a solid.

Provenance & Evidence