Sodium Azide → HCID 60077760, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (37.9 g, 0.58 mol) was added to a solution of [1(S)-(4-fluorobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester (6.0 g, 19.4 mmol) in DMF (400 mL), and the mixture heated at 120° C. for 24 hours. The solvent was removed in vacuo and the residual solid taken up in ethyl acetate (200 ml). The organic phase was washed with 1M Na2CO3 (1×400 ml) and brine (1×400 mL), dried over MgSO4, filtered and the solvent removed in vacuo to give a yellow solid. Purification by column chromatography (SiO2, 6:1 iso-hexane:ethyl acetate) afforded the title compound as a yellow solid (1.96 g) and [1(S)-(4-Azidobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester as an orange solid (0.97 g) (47% combined yield).

Provenance & Evidence