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Water → 4-(2-Benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694904
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HRID 1694904 반응식
CC(C)([O-])C.[K+].[C:7]([O:11][C:12](=[O:37])[NH:13][C:14]([CH3:36])([CH3:35])[CH2:15][N:16]([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)[C:17](=[O:20])[CH2:18]Br)([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+].O>O1CCCC1>[C:7]([O:11][C:12]([N:13]1[CH2:18][C:17](=[O:20])[N:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:15][C:14]1([CH3:36])[CH3:35])=[O:37])([CH3:10])([CH3:9])[CH3:8]
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참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 66645394{2-[(2-Benzyloxyphenyl)-(2-bromoacetyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

생성물 1

HCID 666453984-(2-Benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1.59 g of potassium t-butoxide (14.2 mmol) in tetrahydrofuran (100 ml) was added to a solution of 4.64 g of {2-[(2-benzyloxyphenyl)-(2-bromoacetyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in Example (10b) (9.64 mmol) in tetrahydrofuran (100 ml) under a nitrogen atmosphere and under cooling in a dry ice-acetone bath over 30 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 then water was added, 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:methylene chloride/ethyl acetate=5/1) to obtain 3.42 g of the title compound (yield: 94%).

후처리

  1. temperatureunder cooling in a dry ice-acetone bath over 30 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:methylene chloride/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-efe98a18ead74742a89900f4fd627017
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158790B2

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