Ethyl Acetate → HCID 59128678, compound

Participants

Reaction Steps

A mixture of 28s (40 mg, 0.10 mmol) and 1.0 M TBAF in THF (3 mL) was heated at reflux for 7 h. The reaction mixture was then cooled, poured onto a mixture of AcOEt and saturated aqueous NaHCO3. The layers were separated, the aqueous phase extracted with more AcOEt (2×) then the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by PTLC using 5% MeOH in CH2Cl2 as eluent) to give 29s as a white solid (25.0 mg, 62%); 1H NMR (400 MHz, CDCl3) δ 0.40 (q, J=4.7 Hz, 2H), 0.69 (m, 2H), 1.33 (m, 1H), 3.91 (d, J=7.0 Hz, 2H), 4.00 (s, 3H), 7.36 (d, J=2.5 Hz, 1H), 7.56 (d, J=2.5 Hz, 1H), 7.60 (s, 1H), 7.75 (s, 1H), 8.15 (d, J=2.6 Hz, 1H), 9.14 (bs, NH).

Provenance & Evidence