Reaktion #7125

Reaktionsgleichung

Lithium hydroxide monohydrate

(1R,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid methyl ester

→

product

Ausbeute 80.0%

(1R, 2S)-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid

Ausbeute 80.0%

Lösungsmittel

THF

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   SonstigeOrganic solvents were removed from the mixture in vacuo
3. 3
   WaschenRemaining aqueous was washed with ether (2×15 mL)
4. 4
   ExtraktionMixture was extracted with ethyl acetate (2×20 mL)
5. 5
   WaschenCombined extracts were washed with brine (1×10 mL)
6. 6
   Trocknenthen dried (magnesium sulfate)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

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)−.

Quelle