4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde → (+)-(trans)-2-{4-[({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid

Participants

Reaction Steps

Experimental procedure analogous to that described for synthesis of compounds III-2a and III-3a but instead using (+)-(trans)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate (III-1b) (0.61 g, 2.97 mmol) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde to give 0.30 g (25% yield) of pure title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=7.87 Hz, 2H), 7.65 (d, J=8.24 Hz, 2H), 6.97 (d, J=8.42 Hz, 2H), 6.60 (d, J=8.61 Hz, 2H), 4.46 (s, 2H), 2.51 (m, 1H), 2.50 (s, 3H), 1.79 (m, 1H), 1.59 (m, 1H), 1.35 (m, 1H). ES-MS m/z 432 (MH+). [α]25,D=+128° (chloroform, c=3.8). Product was determined to be 96% ee by chiral SFC according to Method 2.

Provenance & Evidence