Sodium Hydroxide → HCID 178485966, compound

HRID 2118252Notes

Reaction equation

HRID 2118252 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[O:14])[CH3:12])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].OS([O-])(=O)=O.[K+].CCOCC>O1CCOCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:13]([N:11]([CH3:12])[C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[O:14])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 86584777KHSO4 etherHCID 178501224HCID 178501224, compound

Product 1

HCID 178485966HCID 178485966, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.1 g (3.37 mmol) of trans-4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexanecarboxylic acid methyl ester was dissolved in 25 mL of dioxane and treated at 0° C. with 6.7 mL (6.70 mmol, 2 eq) of aqueous 1M NaOH. After 3 h at RT, the reaction was poured into aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to give 0.97 g (92%) of trans-4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexanecarboxylic acid, MS: 310 (M−H−, 1Cl).

Workup

  1. washThe organic phases were washed with aqueous 10% NaCl solution
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-fabd4b61649a44d5a02852fbe31e58d2
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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