反应详情

Lithium hydroxide monohydrate (1.7 mmol) was added to a mixture of (1R,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid methyl ester in THF (8 mL), methanol (8mL) and water (8 mL). Reaction stirred at room temperature overnight. Organic solvents were removed from the mixture in vacuo. Remaining aqueous was washed with ether (2×15 mL). Aqueous layer was made acidic to litmus paper with 1 N hydrochloric acid. Mixture was extracted with ethyl acetate (2×20 mL). Combined extracts were washed with brine (1×10 mL) then dried (magnesium sulfate), filtered and concentrated in vacuo. The product (208 mg) was obtained as a white solid in 80% yield: 1H NMR (300 Mz, CDCl3) δ 7.70 (d, 2 H, J=8.8), 7.48 (d, 4 H, J=8.8), 6.20 (d, 1 H, J=9.5), 3.41 (m, 1 H), 2.81 (dd, 1 H, Jd=4.4, Jd=4.8), 2.03 (m, 1 H), 1.80 (m, 1 H), 1.62 (m, 1 H), 1.44 (m, 2 H), 1.25 (m, 2 H); MS m/e 316 (M−H)−.

1. customReaction
2. customOrganic solvents were removed from the mixture in vacuo
3. washRemaining aqueous was washed with ether (2×15 mL)
4. extractionMixture was extracted with ethyl acetate (2×20 mL)
5. washCombined extracts were washed with brine (1×10 mL)
6. dry with materialthen dried (magnesium sulfate)
7. filtrationfiltered
8. concentrationconcentrated in vacuo