Sodium Hydroxide → 1-[(1-Benzofuran-2-carbonyl)amino]cyclohexane-1-carboxylic acid

HRID 1392381Notes

Reaction equation

HRID 1392381 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([O:21]C)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].[OH-].[Na+]>CO.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([OH:21])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 25605173methyl 1-[N-(benzofuran-2-ylcarbonyl)amino]-1-cyclohexanecarboxylate

Product 1

HCID 246996681-[(1-Benzofuran-2-carbonyl)amino]cyclohexane-1-carboxylic acidYield 49.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the solution of methyl 1-[N-(benzofuran-2-ylcarbonyl)amino]-1-cyclohexanecarboxylate (105.0 g) in 450 ml of methanol, was added 2N-sodium hydroxide solution (170 ml, 0.34 mol). The reaction mixture was refluxed for 23 hours and concentrated to obtain a residue, which was diluted with 400 ml of water and washed with 300 ml of diethyl ether. 6N-hydrochloride was added dropwise to the resulting aqueous layer to adjust the pH of the solution to pH 3. The resulting white solid was filtered and dried to give the titled compound (49.5 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 23 hours
  2. concentrationconcentrated
  3. customto obtain a residue, which
  4. washwashed with 300 ml of diethyl ether
  5. addition6N-hydrochloride was added dropwise to the resulting aqueous layer
  6. filtrationThe resulting white solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-c446747f45f54be6bbc84e5890d8e7a8
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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