Ethyl bromoacetate → 1-Ethoxycarbonylmethyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester

HRID 1253882노트

반응식

HRID 1253882 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[NH:13][C:12](=[O:21])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[NH4+]>CCCCCC.CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12](=[O:21])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

참가 물질

7

반응물 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22632545tert-Butyl 2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate

생성물 1

HCID 686381191-Ethoxycarbonylmethyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester수율 72.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

Sodium hydride (152.6 mg, 3.81 mmol, 60% suspension in mineral oil) was washed with hexane (2×2 mL) in a flame dried round bottomed flask under nitrogen atmosphere. To the resulting free floating powder, was added a solution of 2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (500 mg, 1.90 mmol) in dry DMF (10 mL) at 0° C. The reaction mixture was stirred at this temperature for 1 h. Ethyl bromoacetate (0.21 mL, 1.9 mmol) was added at 0° C. and the reaction mixture was allowed to come to r.t. and stirred overnight. After the completion of the reaction as confirmed by TLC, reaction mixture was cooled to 0° C. and saturated solution of ammonium chloride (3 mL) was added dropwise to the reaction mixture. The crude product was extracted with ethylacetate (3×10 mL). The combined organic layers were dried over Na2SO4 and solvents were removed in vacuo to afford 1-ethoxycarbonylmethyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (480 mg, 72%) as a viscous oil which was used as such without any further purification for the next step.

후처리

  1. customdried round bottomed flask under nitrogen atmosphere
  2. customto come to r.t.
  3. stirringstirred overnight
  4. customAfter the completion of the reaction
  5. customas confirmed by TLC, reaction mixture
  6. extractionThe crude product was extracted with ethylacetate (3×10 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4 and solvents
  8. customwere removed in vacuo

출처 및 근거

ORD 기록
ord-8dfb5d86e7c544c287f0e0b87850a4a8
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455479B2

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