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Ethyl Acetate → {2-[(2-Benzyloxyphenyl)-(2-bromoacetyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

HRID 1694903
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HRID 1694903 반응식
C(=O)(O)[O-].[Na+].[Br:6][CH2:7][C:8](Br)=[O:9].[C:11]([O:15][C:16](=[O:37])[NH:17][C:18]([CH3:36])([CH3:35])[CH2:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:14])([CH3:13])[CH3:12].C(OCC)(=O)C>O>[C:11]([O:15][C:16](=[O:37])[NH:17][C:18]([CH3:36])([CH3:35])[CH2:19][N:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:8](=[O:9])[CH2:7][Br:6])([CH3:14])([CH3:12])[CH3:13]
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 66645956[2-(2-Benzyloxyphenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester

생성물 1

HCID 66645394{2-[(2-Benzyloxyphenyl)-(2-bromoacetyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester수율 92.4%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

1.08 g of sodium bicarbonate (12.9 mmol) and 1.0 ml of bromoacetyl bromide (11.3 mmol) were added to a solution of 4.00 g of [2-(2-benzyloxyphenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester obtained in Example (10a) (10.7 mmol) in a mixed solvent of ethyl acetate (50 ml) and water (50 ml) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. After extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=2/1) to obtain 4.86 g of the title compound (yield: 92%).

후처리

  1. temperaturecooling
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-3784cb5f8db34e28acbebc160b2b5f36
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158790B2

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