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Ammonium Chloride → 2,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694943
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HRID 1694943 반응식
CC(C)([O-])C.[K+].[C:7]([O:11][C:12](=[O:31])[NH:13][C:14]([CH3:30])([CH3:29])[CH2:15][N:16]([C:25](=[O:28])[CH2:26]Br)[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[CH3:24])([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+]>O1CCCC1.O>[C:7]([O:11][C:12]([N:13]1[CH2:26][C:25](=[O:28])[N:16]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[CH3:24])[CH2:15][C:14]1([CH3:30])[CH3:29])=[O:31])([CH3:10])([CH3:9])[CH3:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 66645460{2-[(2-Bromoacetyl)-(5-fluoro-2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

생성물 1

HCID 666457692,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl ester수율 78.7%

시약·촉매·용매 2

HCID 962Water
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2.87 g of potassium t-butoxide (25.6 mmol) in tetrahydrofuran (170 ml) was added to a solution of 7.13 g of {2-[(2-bromoacetyl)-(5-fluoro-2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in Example (70b) (17.0 mmol) in tetrahydrofuran (170 ml) under a nitrogen atmosphere and under cooling in a dry ice-acetone bath over 20 minutes, and the mixture was stirred at the same temperature for 10 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture. The mixture was returned to room temperature and diluted with water, followed by extraction with ethyl acetate. Then, 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 4.5 g of the title compound (yield: 78%).

후처리

  1. temperatureunder cooling in a dry ice-acetone bath over 20 minutes
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-8afd0522f5f04f5ab096451cad557ff6
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158790B2

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