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Methanol → (S)-(-)-N-[[2-Oxo-3-[4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

HRID 840394
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인쇄 미리보기

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HRID 840394 반응식
C(=O)([O-])O.[Na+].[NH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:14][CH:13]=2)=[CH:8][CH2:7]1.[C:29]([O:32][CH2:33][C:34](Cl)=[O:35])(=[O:31])[CH3:30].CO>CC(C)=O.O.ClCCl>[C:29]([O:32][CH2:33][C:34]([N:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)=[O:35])(=[O:31])[CH3:30]
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참가 물질

8

반응물 4

HCID 887MethanolHCID 26297Acetoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 20638827N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

생성물 1

HCID 54460068(S)-(-)-N-[[2-Oxo-3-[4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

시약·촉매·용매 3

HCID 180
Acetone
용매
HCID 962Water용매2회
HCID 6344Dichloromethane용매

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온도
1.5 °C

실험 절차

Sodium hydrogen carbonate (1.89 g) was added to a stirred solution of Example 2 (1.92 g) in a mixture of acetone (25 ml) and water (12.5 ml), and the mixture cooled to 0-3° C. Acetoxyacetyl chloride (1.23 g, 0.97 ml) was added dropwise over 5-10 mins. and the reaction mixture was stirred at 0-5° C. for 30 minutes then allowed to warm to ambient temperature over 1 hour. TLC (10% methanol in dichloromethane) showed complete reaction. The reaction mixture was diluted with water and extracted well with ethyl acetate. The organic phase was washed with brine and dried over anhydrous sodium sulfate. The title compound crystallized during evaporation of the solvent and was triturated with ether (yield=1.70 g, 91%).

후처리

  1. temperatureto warm to ambient temperature over 1 hour
  2. customreaction
  3. extractionextracted well with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe title compound crystallized during evaporation of the solvent
  7. customwas triturated with ether (yield=1.70 g, 91%)

출처 및 근거

ORD 기록
ord-a3ab201a19424518a7cdb1ec0fe0c4d1
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06365751B1

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