Ethyl bromoacetate → 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441219노트

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HRID 441219 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:25]=[CH:24][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15](=[O:23])[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[CH2:31]([O:30][C:28]([CH2:27][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:12]([C:10](=[O:11])[C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:25][CH:24]=2)[CH2:13][CH2:14][C:15]1=[O:23])=[O:29])[CH3:32]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 107337945-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

생성물 1

HCID 106684941-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one수율 67.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a suspension of sodium hydride (60% oil suspension, 154 mg) in tetrahydrofuran (4 ml) was added a solution of 5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (800 mg) in tetrahydrofuran (6 ml) at 0° C. and the mixture was stirred at 0° C. for 5 minutes. To the mixture was added ethyl bromoacetate (472 mg) and then the mixture was stirred at ambient temperature overnight. The reaction was quenched with saturated ammonium chloride aqueous solution and the resultant mixture was diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, and then it was dried over magnesium sulfate. Filtration and evaporation afforded 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (691 mg) as a slightly yellow amorphous.

후처리

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe reaction was quenched with saturated ammonium chloride aqueous solution
  3. additionthe resultant mixture was diluted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialit was dried over magnesium sulfate
  6. filtrationFiltration and evaporation

출처 및 근거

ORD 기록
ord-b3b82ac9982f427d8298181e78db7d1d
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521170

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