Reaktion #7122

Reaktionsgleichung

(1S,2R)-2-aminocyclohexanecarboxylic acid amide

4-chlorobenzenesulfonylchloride

triethylamine

hydrochloric acid

→

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

Ausbeute 53.2%

Lösungsmittel

dichloromethane DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was collected
2. 2
   Waschenwashed with with water (2×500 mL)
3. 3
   workup.ADDITIONHexanes (50 mL) were added to the organic layer
4. 4
   WaschenThe combined mixture was sequentially washed with water (500 mL) and brine (50 mL)
5. 5
   TrocknenThe organic layer was dried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe crude material was purified by silica gel column chromatography (solvent gradient: methanol/chloroform, 0.25% to 5.0%)

Vorschrift

A mixture of (1S,2R)-2-aminocyclohexanecarboxylic acid amide (16.2 mmol), 4-chlorobenzenesulfonylchloride (6.84 g, 32.4 mmol), and triethylamine (20 mL, 143 mmol) were stirred in dichloromethane/DMF (500 mL/100 mL) at room temperature for 6 h. The crude mixture was poured into 1 M hydrochloric acid (500 mL). The organic layer was collected and washed with with water (2×500 mL). Hexanes (50 mL) were added to the organic layer. The combined mixture was sequentially washed with water (500 mL) and brine (50 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (solvent gradient: methanol/chloroform, 0.25% to 5.0%) to afford 2.73 g (53% yield, 5 steps) of (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide. An analytical sample was obtained after recrystallization from ethyl acetate/hexanes: 1H NMR (400 MHz, DMSO-d6) 7.82 (d, 2 H, J=8.5), 7.64 (d, 2 H, J=8.6), 7.57 (d, 1 H, J=7.1), 7.22 (s, 1 H), 6.79 (s, 1 H), 3.43 (m, 1 H), 2.36 (m, 1 H), 1.72 (m, 2 H), 1.46 (m, 3 H), 1.17 (m, 3 H); MS m/e 339.1 (M+Na)+. Anal. calcd. for C13 H17ClN2O3S: C, 49.28; H, 5.40; N, 8.84. Found: C, 49.55; H, 5.24; N, 8.78. Optical rotation: [α]D=−55.8 (c=6.78 mg/mL, DMF).

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