Hydrochloric Acid → HCID 53715534, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the acid from Step 1 (8.29 g, 9.2 mmol) and triethylamine (3.46 g, 34.2 mmol) dissolved in 30 mL of anhydrous toluene, was cooled to 0° C. and treated with diphenylphosphoryl azide (8.23 g, 9.9 mmol). The solution was maintained at 0° C. for 45 minutes and warmed to room temperature for 3.75 hours. The reaction was poured into water, extracted with ether, dried over magnesium sulfate, and concentrated in vacuo to remove the ether. The remaining toluene solution was heated to 110° C. for 1 hour. Tert-Butyl alcohol (6 mL, 63 mmol) was added to the reaction mixture, after an additional twenty minutes, concentrated hydrochloric acid (2.6 mL) was cautiously added and the reaction maintained at 90° C. overnight (16 hours). After cooling the solution to room temperature, the mixture was concentrated in vacuo and the residue taken up in ethyl acetate, washed successively with water, sat. aq. NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a yellow solid (6.44 g, 86%): mp 54°-61° C. 1H NMR (CDCl3) 300 MHz 7.69 (d, J=7.7 Hz, 1H), 7.36 (m, 1H), 7.20-7.26 (m, 4H), 7.16 (d, J=8.5 Hz, 2H), 4.17 (s, 2H), 2.46 (s, 3H), 2.44 (s, 3H). Mass spectrum M+H=257.

Provenance & Evidence