Hydrochloric Acid → [9-Benzyl-5-carbamoyl-1-chlorocarbazol-4-yl]oxyacetic acid methyl ester

HRID 51450Notes

Reaction equation

HRID 51450 reaction equation
[CH3:1][O:2][C:3](=[O:23])[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])[NH:11][C:10]=2[C:9]([Cl:22])=[CH:8][CH:7]=1.[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:23])[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]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:10]=2[C:9]([Cl:22])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 69868854[5-Carbamoyl-1-chlorocarbazol-4-yl]oxyacetic acid methyl ester

Product 1

HCID 69869145[9-Benzyl-5-carbamoyl-1-chlorocarbazol-4-yl]oxyacetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 78 mg of [5-carbamoyl-1-chlorocarbazol-4-yl]oxyacetic acid methyl ester in 0.8 ml of dry dimethylformamide was added to 10 mg sodium hydride (60% in mineral oil) in 0.2 ml of dimethylformamide and stirred for 15 minutes. Benzyl bromide (0.031 ml) was then added and the reaction was stirred overnight. The reaction mixture was poured into water and acidified with 1 ml of 1 N HCl solution and extracted twice with ethyl acetate. The extracts were washed with water (3×) and then with brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with methanol/0-2% in dichloromethane to afford 40 mg of the subtitle compound. ESIMS m/e 423 (M++1) 425 (M++3) NMR (300 MHz, CDCl3): δ7.43-7.22 (m, 7H); 7.06 (d, J=7.3, 2H); 6.51 (d, J=8.6, 1H); 6.05 (s, 2H); 5.80 (br, 2H); 4.88 (s, 2H); 3.83 (s, 3H).

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed with water (3×)
  4. dry with materialwith brine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with methanol/0-2% in dichloromethane

Sources & evidence

ORD record
ord-b4f58d9683c44440868d223fd21b37a6
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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