Sodium hydride → Ethyl 4-[3-(2-tert-butoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]benzoate

HRID 1921199노트

반응식

HRID 1921199 반응식
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[NH:3]1.[H-].[Na+].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CN(C=O)C>[C:29]([O:28][C:26](=[O:27])[CH2:25][N:3]1[C:4]2[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=2[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[C:2]1=[O:1])([CH3:32])([CH3:31])[CH3:30]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 18449399Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

생성물 1

HCID 18449400Ethyl 4-[3-(2-tert-butoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate from Step C (590 mg, 2.09 mmol) in DMF (10 mL) at 0° C. was added sodium hydride (104 mg of a 60% dispersion in mineral oil, 2.60 mmol). The mixture was stirred for 5 min, then tert-butyl bromoacetate (489 mg, 2.51 mmol) was added and stirring was continued for 3 h. The reaction mixture was partitioned between EtOAc (200 mL) and H2O (100 mL). The organic layer was washed with H2O (50 mL), then brine (50 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=397 (M+1).

후처리

  1. stirringstirring
  2. waitwas continued for 3 h
  3. customThe reaction mixture was partitioned between EtOAc (200 mL) and H2O (100 mL)
  4. washThe organic layer was washed with H2O (50 mL)
  5. dry with materialbrine (50 mL), then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

출처 및 근거

ORD 기록
ord-719b4d1c1352460a9c6b5f294525a24a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173655B2

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