Potassium Hydroxide → HCID 87955284, compound

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Reaction Steps

The compound of Example 137 was hydrolyzed using an excess of aqueous 10% NaOH in methanol, stirring overnight. The reaction mixture was concentrated in vacuo, water was added, and the solution was extracted with ether. The mixture was acidified; the resultant solid was collected by filtration and dried overnight in a vacuum oven, giving a white solid, m.p. 166-171C. 1H-NMR (DMSO 300 MHz) δ 1.17 (t, J=7 Hz, 3H), broad peaks totaling 9 protons at 1.32-1.48, 1.51-1.78, 1.90-2.04, 2.25-2.50, 2.80-2.90, 2.95-3.17, 3.45-3.51, 3.95-4.19, 4.41-4.51, 4.06 (q, J=7 Hz, 1H), 6.80 (d, J=9 Hz, 1H), 7.01 (t, J=7 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 7.26-7.40 (m, 2H), 7.40-7.48 (m, 1H), 7.51 (dd, J=9 Hz, 2 Hz, 1H), 7.99 (d, J=9 Hz, 1H). Anal. Calcd. for C23H24ClNO4S: C, 61.94; H, 5.42; N, 3.14. Found: C, 61.75; H, 5.65; N, 3.15. The resultant acid (303 mg, 0.631 mmol) was dissolved in 3 mL MeOH. A KOH solution (38 mg, 0.595 mmol, of 87.6% KOH) in 1 ml MeOH was added. The resulting solution was concentrated in vacuo, and 5 mL ether was added. The mixture was stirred for one hour to form a powder, which was filtered and dried in the vacuum oven at 60C to yield 307 mg of a solid, water soluble product.

Provenance & Evidence