Triethylamine → HCID 13799233, compound

Participants

Reaction Steps

To a stirred solution of 3α,12α-diformyloxy-7-oxo-5β-cholan-24-oic acid (19 g) in 400 ml of ethyl acetate were added 8.0 ml of triethylamine, a solution of 6.0 ml of 2-amino-2-methyl-1-propanol in 50 ml of ethyl acetate, and 15 g of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline and the mixture was refluxed for 5 hrs. After cooling to room temperature, the reaction mixture was washed successively with water (50 ml×1), 1N HCl solution (50 ml×4), water (50 ml×1), 5% NaHCO3 solution (50 ml×2), and then water to neutrality (50 ml×3). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated in vacuo to give an oily residue (21.5 g) which could not be crystallized. PMR (δ ppm): 0.66 (3H, s, 18--CH3), 0.85 (3H, d, J=6 Hz, 21--CH3), 1.08 (3H, s, 19--CH3), 1.53 (6H, s, --C(CH3)2 --), 3.88 (2H, s, --CH2OH), 4.71 (1H, m, 3β--H), 5.22 (1H, m, 12β--H), 7.58 (1H, s, --NH--), 8.03 and 8.18 (2H, s, 2×--COH).

Provenance & Evidence