Diisopropylethylamine → (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate

Participants

Reaction Steps

To a solution of (R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid (D3) (100 mg, 1 equiv), HATU (220 mg, 1.5 equiv), and DIEA (0.67 mL, 10 equiv) in DCM (5 mL) was added 2-amino-1-(4-(octyloxy)-3-(trifluoromethyl)phenyl)ethanone hydrochloride (D2) (142 mg, 1.0 equivalents). The solvent removed in vacuo and the product was purified with silica gel column chromatography using the Combi-Flash system (Hex:EtOAc). This resulted in a colourless, thick oil which was dissolved in toluene (5 mL) with Lawesson's reagent (280 mg, 3 equiv). The resultant mixture was heated at 120° C. for 2 hours to produce the title product as a colourless oil 41% yield (90 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