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Triethylamine → tert-butyl 1-(3-methylbut-2-enoyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate

HRID 1754540
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HRID 1754540 반응식
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:26][C:27]([CH3:32])=[CH:28][C:29](Cl)=[O:30]>ClCCl>[CH3:26][C:27]([CH3:32])=[CH:28][C:29]([N:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH2:2]1)=[O:30]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chlorideHCID 27718261,2,3,5-Tetrahydro-benzo(e)(1,4)diazepine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 86712747tert-butyl 1-(3-methylbut-2-enoyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate수율 95.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1 g (4.04 mmol) of tert-butyl 2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate was dissolved in 20 mL of dichloromethane and treated with 1.54 mL (8.86 mL) of triethylamine followed by 0.53 mL (4.83 mmol) of 3-methylbut-2-enoyl chloride. The reaction mixture was stirred over night at room temperature, poured onto water (50 mL) and extracted three times with 50 mL of dichloromethane each. The organic phases were combined, washed with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica (eluent: 5-10% methanol in dichloromethane) to yield 1.27 g of the title compound as a white solid.

후처리

  1. additionpoured onto water (50 mL)
  2. extractionextracted three times with 50 mL of dichloromethane each
  3. washwashed with a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica (eluent: 5-10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-b7b66118fd10492088c5f4a6bcbb7448
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09169253B2

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