Methanol → HCID 10382175, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 4A (0.09 g, 0.24 mmol), Pd(dppf)Cl2 (5 mol %), and CuI (6 mol %) was sealed using a crimper and treated with a solution of isobutylzinc bromide (0.5M in THF, 0.96 mL, 0.48 mmol). The reaction was heated in a single-mode microwave cavity in the Smith synthesizer at 160° C. for 600 seconds and filtered through a 1 micron PTFE syringe filter. The filtrate was concentrated, dissolved in 1:1 CH3OH:DMSO (1.5 mL), and purified using a C18 reverse-phase HPLC with acetonitrile/water/1% TFA. The purified ester was saponified by treatment with 10 equivalents of 2N NaOH in 1:1 CH3OH:THF at 70° C. for 48 hours. The mixture was extracted with ethyl acetate and the extract was concentrated to provide the desired product. MS (ESI(+)) m/e 334 (M+H)+, 351 (M+NH4)+, 356 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) δ 10.90 (s, 1H), 7.80 (m, 2H), 7.40 (m, 3H), 7.10 (s, 1H), 6.80 (m, 1H), 6.50 (m, 1H), 2.20 (d, 2H), 1.70 (m, 1H), 0.80 (d, 6H).

Provenance & Evidence