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

HRID 1270367ノート

反応式

HRID 1270367 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-76a7bb29f56743408c4acc6954ebb735
出典データセット
uspto-grants-2007_04
特許番号
US07202251B2

反応ノート

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