Sodium Hydroxide → 1-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acid

HRID 1392409Notes

Reaction equation

HRID 1392409 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([O:17]C)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].[OH-].[Na+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17464840methyl 1-[N-(furan-2-ylcarbonyl)amino]-1-cyclohexanecarboxylate

Product 1

HCID 174552541-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of methyl 1-[N-(furan-2-ylcarbonyl)amino]-1-cyclohexanecarboxylate (9.6 g) obtained in Step 1 in 100 ml of methanol, was added 2N-sodium hydroxide solution (50 ml). The reaction mixture was refluxed for 3 hours and concentrated. The resulting residue was diluted with 150 ml of water and washed with 100 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 (6.1 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. concentrationconcentrated
  3. additionThe resulting residue was diluted with 150 ml of water
  4. washwashed with 100 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-799b78f15edb4ce1ac8f00e026c29467
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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