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

HRID 1091961Notes

Reaction equation

HRID 1091961 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+].[C:17]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>O1CCOCC1>[C:17]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:20]([S:23]([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:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 2724640trans-2-Aminocyclohexanecarboxylic acid

Product 1

HCID 66588543(trans)-2-[[(4-Biphenyl)sulfonyl]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 biphenyl-4-sulfonyl chloride (2.02 g, 8.0 mmol) in dioxane:water (70:35 mL) in the same manner as described in Example 1. The yield was 1.48 g (59%), the melting point was 220-222° C., and mass spectrometry revealed a molecular ion peak (MH)+ at m/z 360.

Sources & evidence

ORD record
ord-cc4de97506db4be5bf7ffcc4f31a10e9
Source dataset
uspto-grants-2012_03
Patent number
US08129406B2

Reaction notes

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