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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
ノート
印刷プレビュー

反応式

HRID 840394 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180
Acetone
溶媒
HCID 962Water溶媒2 回
HCID 6344Dichloromethane溶媒

反応条件

温度
1.5 °C

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-a3ab201a19424518a7cdb1ec0fe0c4d1
出典データセット
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06365751B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート