Sodium Hydroxide → [9-Benzyl-5-carbamoyl-1-methylcarbazol-4-yl]oxyacetic acid

HRID 567356Notes

Reaction equation

HRID 567356 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:19](=[O:21])[NH2:20])[N:11]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]=2[C:9]([CH3:29])=[CH:8][CH:7]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:22]([N:11]1[C:10]2[C:9]([CH3:29])=[CH:8][CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][C:16]=2[C:19](=[O:21])[NH2:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69867929HCID 69867929, compound

Product 1

HCID 10271590[9-Benzyl-5-carbamoyl-1-methylcarbazol-4-yl]oxyacetic acidYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 32 mg (0.0795 mmol) of [9-benzyl-5-carbamoyl-1-methylcarbazol-4-yl]oxyacetic acid methyl ester in 1 ml of tetrahydrofuran and 3.5 ml of methanol was treated with 0.3 ml of an aqueous 2 N sodium hydroxide solution and stirred overnight at room temperature. The solvent was evaporated and the residue was partitioned between 1:1 ethyl acetate/tetrahydrofuran and 0.2 N HCl solution. After another extraction with 1:1 ethyl acetate/tetrahydrofuran, the extracts were washed with brine, dried over magnesium sulfate and concentrated to afford (27 mg) of the title compound. mp. 253-254° C. ESIMS m/e 389 (M++1), 387 (M+−1) NMR (300 MHz, d6-DMSO): δ 12.83 (br, 1H); 7.75 (br, 1H); 7.53 (d, J=8.2, 1H); 7.41-7.34 (m, 2H); 7.28-7.17 (m, 3H); 7.07 (m, 2H); 6.90 (d, J=7.2, 2H); 6.49 (d, J=8.1, 1H); 5.89 (s, 2H); 4.79 (s, 2H); 2.52 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between 1:1 ethyl acetate/tetrahydrofuran and 0.2 N HCl solution
  3. extractionAfter another extraction with 1:1 ethyl acetate/tetrahydrofuran
  4. washthe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db6fbd4acd1b413890f619bca1cd4fa5
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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