Water → (trans)-2-[(4-Phenoxybenzenesulfonyl)amino]cyclohexanecarboxylic acid

HRID 1091962Notes

Reaction equation

HRID 1091962 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(=O)([O-])[O-].[Na+].[Na+].[O:17]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCOCC1>[O:17]([C:24]1[CH:29]=[CH:28][C:27]([S:30]([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:32])=[O:31])=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2724640trans-2-Aminocyclohexanecarboxylic acidHCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Product 1

HCID 66588486(trans)-2-[(4-Phenoxybenzenesulfonyl)amino]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

This compound was prepared from trans-2-amino-1-cyclohexanecarboxylic acid (1.0 g, 7.0 mmol) by reacting it with sodium carbonate (1.48 g, 14.0 mmol) and 4-phenoxybenzenesulfonyl chloride (2.25 g, 8.38 mmol) in dioxane:water (40:20 mL) in the same manner as described in Example 1. This yielded 1.275 g (48%). The melting point was 192-194° C. Mass spectrometry revealed a molecular ion (MH)+ peak at m/z 376.

Sources & evidence

ORD record
ord-f6f59a4854ea43aeb5a3cd6e2b5a29b9
Source dataset
uspto-grants-2012_03
Patent number
US08129406B2

Reaction notes

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