Diisopropylethylamine → HCID 53349361, compound

Participants

Reaction Steps

(R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid (D7) (210 mg, 0.81 mmol), HATU (372 mg, 0.98 mmol), diisopropylethyl amine (DIEA) (0.705 mL, 4.1 mmol), CH2Cl2-DMF and 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (D6) (270 mg, 0.81 mmol) were mixed together. The reaction was condensed, diluted with ethyl acetate, washed with water and brine, and condensed again. Another batch was made using this method with (D7) (0.1 mmol), HATU (46 mg, 0.12 mmol), DIEA (87 mL, 0.5 mmol), CH2Cl2-DMF and 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (D6) (>6 mg, 0.1 mmol). The batches were chromatographed and combined to provide the title product (428 mg). MS (ESI): 573.84 (MH+); 1H NMR (400 MHz, CDCl3) δ 9.43 (br, 2H), 8.06 (d, 1H, J=2.0 Hz), 7.94 (dd, 1H, J=8.8 Hz, J=2.0 Hz), 6.96 (d, 1H, J=8.8 Hz), 4.52 (br, 1H), 4.07 (t, 2H, J=6.4 Hz), 3.76 (br, 1H), 1.82 (m, 2H), 1.67 (s, 6H), 1.57 (s, 3H), 1.51 (s, 9H), 1.51-1.43 (m, 4H), 1.38-1.24 (m, 6H), 0.88 (t, 3H, J=7.2 Hz).

Provenance & Evidence