HCID 178457031, compound → HCID 178457030, compound

Participants

Reaction Conditions

Reaction Steps

The resultant more polar methyl ester from Example 217A (10.4 mg, 19.5 μmol) was dissolved in 0.1 mL of methanol and 0.09 mL 1.0M aqueous sodium hydroxide. The solution was heated (in a sealed vial) at 80° C. for 28 hours, then cooled and concentrated to an aqueous residue by means of a stream of nitrogen. The residue was partitioned between 5 mL of methylene chloride and 2 mL 1.0M aqueous sodium hydrogen sulfate, then the aqueous phase was extracted with 2×2 mL methylene chloride. The combined organic phases were washed with 2 mL brine, dried through a plug of sodium sulfate, and evaporated under high vacuum to provide a colorless glass. Purification by preparative TLC (1% HOAc in 1:1 CH2Cl2 -EtOAc) produced 9.0 mg (17.3 μmol, 89%) of the title compound as a colorless glass. m.p. 68°-82° C. 1H NMR (CDCl3, 300 MHz) d 0.88 (t, J=7.5 Hz, 3H), 1.37-1.52 (br m, 2H), 3.21-3.31 (br m, 2H), 4.12 (s, 2H), 5.49 (s, 2H), 6.65 (d, J=7.5 Hz, 2H), 6.77 (d, J=9 Hz, 1H), 6.86 (d, J= 7.5 Hz, 2H), 7.20-7.55 (m, 10H), 7.84 (dd, J=1.5, 7 Hz, 1H), 8.25 (d, J=7.5 Hz, 1H). MS (DCl/NH3) m/e 521 (M+H)+.

Provenance & Evidence