Thiazolidine → HCID 19894090, compound

Participants

Reaction Steps

Dicyclohexyl carbodiimide (DCC, 3.4 g, 16.7 mmole) was added to a solution of the thiazolidine acid prepared as described above in step 1 (2.3 g, 11 mmole), 3-aminobenzophenone (2.2 g, 11 mmole), and 1-hydroxybenzotriazole hydrate (HOBT, 1.5 g, 11 mmole) in dimethylformamide (25 mL). The reaction mixture was stirred for 20 hours at room temperature and then water (5 mL) was added to quench the excess DCC. Twenty minutes later ethylacetate was added and the mixture filtered to remove dicyclohexyl urea. The filtrate was washed with saturated sodium bicarbonate, water and saturated sodium chloride the dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed on 200 g silica gel eluting with 5% methanol in methylene chloride to yield the desired product (1.7 g, 40%). MS (DCI-NH3) m/e:386 (M+1)+ ; 1H NMR (CDCl3) d 3.43-3.62 (c, 1.5H), 3.82 (dd, 0.5H, J=4.5, 12), 4.20-4.30 (c, 0.5H), 4.54 (m, 0.5H, J=4.0), 4.98 (d, 0.5H, J=12), 5.72 (bs, 0.5H), 7.32-7.62 (c, 7H) 7.76-8.05 (c, 6H), 8.53 (dd, 0.5H, J=2,5), 8.62 (dd, 0.5H, J=2,5), 8.80 (b s, 0.5H), 9.28 (s, 0.5H).

Provenance & Evidence