Acetyl chloride → HCID 10440854, compound

Participants

Reaction Conditions

Reaction Steps

NEt3 (0.16 mL, 1.15 mmol) was added to (11) (0.87 g, 0.98 mmol) in CH2Cl2 (40 mL) and the solution was cooled to 0° C. Acetyl chloride (0.074M in CH2Cl2, 14 mL, 1.04 mmol) was added by syringe over 4 minutes and stirring was continued (0° C. to room temperature) for 24 hours. The aqueous phase was extracted with CH2Cl2 (4×50 mL) and the organic phase was washed with 40 mL portions of cold 0.25M citric acid, 5% NaHCO3 and H2O. Solvent removal and flash column chromatography with 60% acetone/hexane gave 0.79 g (87%) of (12) as an oil: 300 MHz NMR δ 1.23-1.69 (m+s, 27 H), 2.09 (s, 3 H), 2.44-2.53 (m, 4 H), 2.76-2.84 (m, 6 H), 3.03-3.24 (m, 6 H), 3.57-3.68 (m, 6 H), 4.7 (br s, 1 H), 4.81 (s, 2 H), 4.85 and 4.86 (2 s, 4 H), 6.35 (br s, 1 H), 7.38 (s, 15 H). Anal. calcd. for C51H74N6O10 : C, 65.78; H, 8.01; N, 9.03. Found: C, 65.89; H, 8.04; N, 8.95.

Provenance & Evidence