Sodium Hydroxide → HCID 10293915, compound

HRID 51440Notes

Reaction equation

HRID 51440 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:7]=1[C:8]1[CH:9]([C:27](=[O:29])[NH2:28])[CH2:10][CH2:11][CH2:12][C:13]=1[N:14]2[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:20]([N:14]1[C:13]2[CH2:12][CH2:11][CH2:10][CH:9]([C:27](=[O:29])[NH2:28])[C:8]=2[C:7]2[C:15]1=[C:16]([CH3:19])[CH:17]=[CH:18][C:6]=2[O:5][CH2:4][C:3]([OH:30])=[O:2])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69868433HCID 69868433, compound

Product 1

HCID 10293915HCID 10293915, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 64 mg (0.157 mmol) of [9-benzyl-4-carbamoyl-8-methyl-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid methyl ester in 2 ml of tetrahydrofuran and 7 ml of methanol was treated with 0.5 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 ethyl acetate and 1 N HCl solution. After another extraction with ethyl acetate, the extracts were washed with brine, dried over magnesium sulfate and concentrated to afford a quantitative yield (62 mg) of the title compound. ESIMS m/e 393 (M++1), 391 (M+−1). NMR (300 MHz, d6-DMSO): δ12.98 (br, 1H); 7.30-7.18 (m, 3H); 6.82 (d+br, J=7.0, 3H); 6.73 (br, 1H); 6.59 (d, J=7.9,1H); 6.26 (d, J=7.9, 1H); 5.53 and 5.45 (ABq, J=18.1, 2H); 4.62 (s, 2H); 3.96 (br, 1H); 2.63 (m, 1H); 2.43 (m, 1H); 2.34 (s, 3H); 2.04 (m, 2H); 1.78 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-c960cccb26b64a0f83c6c29b42c66b03
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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