Sodium hydride → {9-[(Phenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester

HRID 51320노트

반응식

HRID 51320 반응식
[H-].[Na+].[C:3]1([CH2:9][N:10]2[C:22]3[CH:21]=[C:20]([CH3:23])[CH:19]=[C:18]([OH:24])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][C:15]=3[C:25](=[O:27])[NH2:26])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C.C1COCC1.C(OCC)(=O)C>[C:3]1([CH2:9][N:10]2[C:22]3[CH:21]=[C:20]([CH3:23])[CH:19]=[C:18]([O:24][CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][C:15]=3[C:25](=[O:27])[NH2:26])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 227393719-[(Phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole

생성물 1

HCID 21304100{9-[(Phenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester수율 75%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

60% Sodium hydride in mineral oil (30.4 mg, 0.76 mM) was added to a solution of 9-[(phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole (202 mg, 0.61 mM) in 21 mL DMF and 4.6 ml THF. After 10 minutes, methyl bromoacetate (77 μl, 0.482 mM) was added and the resultant mixture stirred at room temperature for 1.25 hours. The mixture was diluted with ethyl acetate and washed with H2O. The aqueous layer was extracted with ethyl acetate. The combined organic layers were extracted with saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (elution with ethyl acetate) to afford 184 mg (75%) of {9-[(phenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester. 1H NMR (DMSO-d6) δ7.55 (d, 1H, J=8 Hz), 7.5 (bs, 1H), 7.4-7.15 (m, 9H), 6.45 (s, 1H), 5.7 (s, 2H), 4.9 (s, 2H), 3.75 (s, 3H), 2.4 (s, 3H). MS (FD) m/e 386, 403.

후처리

  1. washwashed with H2O
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined organic layers were extracted with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (elution with ethyl acetate)

출처 및 근거

ORD 기록
ord-bbfccb42ccf44f36906f23892f8daaf7
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713645B1

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