Acetic Acid → HCID 22184676, compound

Participants

Reaction Steps

Acyl oxazolidinone (1.28 g, 2.62 mmol) from Step G in 30 mL of THF at −78° C. was treated with 5.8 mL (2.89 mmol) of a 1.5 M solution of potassium hexamethyldisilylamide in toluene followed by 973 mg (3.14 mmol) of trisyl azide in 6 mL of THF and quenched by the addition of 634 mg (10.5 mmol) of acetic acid according to the procedure of D. A. Evans et al., J. Amer. Chem. Soc. 1990, 10, 4011. Purification by Biotage chromatography on silica gel (25% ether/hexane) provided 720 mg (52%) of the title compound. 1H NMR (500 MHz, CDCl3) δ 7.39–7.24 9 (m, 5H), 5.12 (d, 0.3H, J=8.7 Hz), 4.97 (d, 0.7H, J=7.5 Hz), 4.72 (m, 1H), 4.25 (m, 2H), 3.61 (d, 0.6H, J=7 Hz), 3.51 (d, 1.4H, J=5.9 Hz), 3.33 (dd, 1H, J=3 and 4 Hz), 2.87 (dt, 1H, J=3 and 10 Hz), 2.0–1.4 (m, 8H), 1.07–0.9 (m and d, 24H).

Provenance & Evidence