Dicyclohexylcarbodiimide → 4-(3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-1-(2-thioxo-thiazolidin-3-yl)-pentan-1-one

Participants

Reaction Steps

To a vigorously stirred solution of cholic acid (1 g, 2.6 mmol) in CH2Cl2 (60 mL) was added DCC (684 mg, 3.6 mmol), 2-mercaptothiazoline (354 mg, 3 mmol), and catalytic amount (40 mg) of N,N-dimethyl amino pyridine (DMAP). The reaction mixture was stirred for 24 h at room temperature at which time the reaction mixture was transferred to a separate-funnel and sequentially washed with 0.5N NaOH solution (100 mL×2), and 0.1N HCl (100 mL×2). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide pure yellow solid 2 (1.07 g, 82%). 1H NMR (CDCl3) δ 0.68 (s, 3H), 0.90 (s, 3H), 0.98 (d, 3H), 1.10-1.95 (m, 23H), 3.25-3.35 (m, 4H), 3.53-3.67 (m, 1H), 3.98 (s, 1H), 4.57 (t, 2H); 13C NMR (CDCl3) δ12.73, 17.49, 23.16, 23.76, 26.17, 27.21, 27.63, 28.33, 28.60, 30.40, 30.74, 33.52, 34.11, 35.32, 35.48, 35.87, 36.00, 36.40, 42.08, 46.52, 47.44, 48.09, 53.59, 56.16, 71.53, 72.99, 175.35, 201.52. HRMS (Positive ion FAB) Calcd for C27H44N3O2 [M+H]+ m/z 494.2763. Found: [M+H]+ m/z 494.2744.

Provenance & Evidence