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Water → (2R)-1-Acetoxy-2-acetylamino-2-methyl-4-(1-ethylpyrrol-2-yl)butane

HRID 562642
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HRID 562642 반응식
[NH2:1][C@:2]([CH3:14])([CH2:5][CH2:6][C:7]1[N:8]([CH2:12][CH3:13])[CH:9]=[CH:10][CH:11]=1)[CH2:3][OH:4].C(N([CH2:20][CH3:21])CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23].[OH2:29]>ClCCl.CN(C)C1C=CN=CC=1>[C:22]([O:4][CH2:3][C@@:2]([NH:1][C:20](=[O:29])[CH3:21])([CH3:14])[CH2:5][CH2:6][C:7]1[N:8]([CH2:12][CH3:13])[CH:9]=[CH:10][CH:11]=1)(=[O:24])[CH3:23]
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참가 물질

7

반응물 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18448118(2R)-2-amino-2-methyl-4-(1-ethylpyrrol-2-yl)butan-1-ol

생성물 1

HCID 66673196(2R)-1-Acetoxy-2-acetylamino-2-methyl-4-(1-ethylpyrrol-2-yl)butane수율 96%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

To a solution of (2R)-2-amino-2-methyl-4-(1-ethylpyrrol-2-yl)butan-1-ol 1/2 D-(−)tartrate (2.7 g, 7.80 mmol) obtained in Reference example (24a) in dichloromethane (30 ml) were added successively triethylamine (17.0 ml, 122 mmol), acetic anhydride (7.6 ml, 80.4 mmol) and 4-dimethylaminopyridine (20 mg, 0.16 mmol), and the resulting mixture was stirred at room temperature for 3.5 hours. After stirring, water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was washed successively with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using ethyl acetate as the eluent to afford the title compound (2.2 g, yield: 96%).

후처리

  1. stirringAfter stirring
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. washThe extract was washed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-b6c5afd421b744b08a8826343903053e
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067396B2

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