Diisopropylethylamine → (R)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)oxazolidine-3-carboxylate

Participants

Reaction Steps

To a solution of protected oxazolidine-4-carboxylic acid 4 (176 mg, 1 equivalents), HATU (310 mg, 1.2 equivalents), and DIEA (1.2 mL, 10 equivalents) in CH2CL2/DMF (1:1, 10 mL) was added amino-acetophenone 3 (250 mg, 1.0 equivalents). The resultant mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with 10% NH4Cl (2×50 mL) and saturated NaCl (1×50 mL). The solvent removed in vacuo and the product was obtained, silica gel column chromatography using the Combi-Flash system (Hex:EtOAc), as a white solid in 40% yield (185 mg). TLC (1:2 EtOAc:Hex), Rf=0.3; MS (ESI, M+Na)=572.99; 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 8.11 (d, 1H, J=8.4 Hz), 7.05 (d, 1H, J=8.4 Hz), 4.62-4.79 (m, 2H), 4.13 (t, 2H, J=6.4 Hz), 3.28 (br s, 1H), 1.22-1.90 (m, 30H), 0.89 (t, 3H, J=6.4 Hz).

Provenance & Evidence