4-Methoxybenzenesulfonyl chloride → (trans)-2-(4-Methoxybenzenesulfonyl)aminocyclohexanecarboxylic acid

HRID 2268280Notes

Reaction equation

HRID 2268280 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>O1CCOCC1.O.CCCCC>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[C:8]([OH:10])=[O:9])(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2724640trans-2-Aminocyclohexanecarboxylic acid

Product 1

HCID 15430592(trans)-2-(4-Methoxybenzenesulfonyl)aminocyclohexanecarboxylic acidYield 52.5%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To a room temperature solution of 1 g (6.8 mmol) of trans-2-amino-1-cyclohexylcarboxylic acid in 50 ml of dioxane: H2O (1:1) containing 1.7 ml (12.2 mmol) of triethylamine was added 1.54 g (7.46 mmol) of 4-methoxybenzenesulfonyl chloride. The mixture was stirred at 25° C. for 18 h. The resulting mixture was diluted with pentane to afford 1.119 g (51%) of the desired sulfonamide product as a white solid. 1H NMR(DMSO-d6): 7.7 ppm (dd, 2H, Ar), 7.4 ppm (d, 1H, NH), 7.0 ppm (dd, 2H, Ar), 3.8 ppm (s, 3H, OMe), 3.5 ppm (m, 1H, N—CH), 1.0-1.7 ppm (m, 9H, hydrocarbon).

Sources & evidence

ORD record
ord-e0221a0b16bb480cb3fecd442cfdecea
Source dataset
uspto-grants-2001_12
Patent number
US06326516B1

Reaction notes

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