Acetic Anhydride → HCID 59607544, compound

Participants

Reaction Steps

A solution of (R)-ethyl 4-(3′-aminobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate (70.5 mg, 0.171 mmol), Et3N (0.027 ml, 0.205 mmol) and Ac2O (0.019 ml, 0.205 mmol) in DCM (1.7 ml) is allowed to stir at room temperature for 65 hours. The reaction mixture is diluted with water. The products are extracted with DCM in a phase separator and concentrated to give crude (98 mg). The crude is purified by silica gel flash column chromatography (eluent: DCM/MeOH=10:1) to give (R)-ethyl 4-(3′-acetamidobiphenyl-4-yl)-3-(4-methoxy-4-oxobutanamido)butanoate (71.5 mg); HPLC retention time=1.45 minutes (condition D); MS (m+1)=455.4; 1H NMR (400 MHz, CD3CN, mixture of rotamers, data for major rotamer) δ ppm 1.21 (t, J=7.1 Hz, 3 H) 2.07 (s, 3 H) 2.31-2.34 (m, 2 H) 2.40-2.51 (m, 4 H) 2.82-2.84 (m, 2 H) 3.58 (s, 3 H) 4.07 (q, J=7.1 Hz, 2 H) 4.34-4.43 (m, 1 H) 6.46 (br d, J=8.9 Hz, 1 H) 7.28-7.39 (m, 4 H) 7.52-7.54 (m, 3 H) 7.80 (s, 1 H) 8.37 (br s, 1 H).

Provenance & Evidence