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

HRID 1694903
ノート
印刷プレビュー

反応式

HRID 1694903 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3784cb5f8db34e28acbebc160b2b5f36
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158790B2

反応ノート

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