Hydrochloric Acid → HCID 44177830, compound

Participants

Reaction Steps

A solution of 137 mg (0.31 mmol) of ester 16 in 2 mL of THF was hydrolyzed with 800 uL (0.40 mmol) of aqueous lithium hydroxide (0.5M) and 1 mL of methanol at 25° C. for 6 h. The mixture was acidified to pH 5-6 by addition of 400 uL of 1.0M hydrochloric acid and the residual water was removed in vacuo. The residual products were purified by FCC on 10 g of silica gel eluted with 8% methanol:92% EtOAc, then 10% methanol:90% ethyl acetate. Isolated from appropriate fractions was 110 mg of free acid 17 as an oil (88% yield); 1H NMR (acetone-d6): 1.13 (d, J=6.3 Hz, 3H), 1.16-1.68 (m, 13H), 1.86 (m, 1H), 2.0-2.24 (m, 3H), 2.29 (t, J=7.5 Hz, 2H), 3.73 (m, 1H), 4.09 (m, 3H), 5.56 (m, 2H). LC-MS 373.3 [M++1-H2O].

Provenance & Evidence