Water → (S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate

HRID 1487173ノート

反応式

HRID 1487173 の反応式
CS(O[C@@H:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)=O.[C:13]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[F-].[Cs+].O>CN(C=O)C>[CH:14]([C:13]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@@H:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:12]

参加物

6

反応物 4

HCID 962WaterHCID 25953Cesium fluorideHCID 84754Dibenzyl malonateHCID 6364515ethyl (2S)-2-methylsulfonyloxypropanoate

生成物 1

HCID 86699671(S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of (S)-ethyl 2-(methylsulfonyloxy)propanoate (28.4 g, 0.1 mol) in N,N′-dimethylformamide (400 mL) was added dibenzyl malonate (23.5 g, 0.12 mol) and cesium fluoride (15.2 g, 0.1 mol). The mixture was heated at 50° C. for 2 days. After cooled to room temperature, the mixture was poured into water and then extracted with ethyl acetate. The organic phases were combined, washed with brine, water and dried over anhydrous sodium sulfate, and then concentrated to afford the crude product (S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate, which was purified by silica gel chromatography (23 g, yield 60%).

後処理

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine, water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-110d67e3c77a4d46828757eda998cc6b
出典データセット
uspto-grants-2016_08
特許番号
US09428508B2

反応ノート

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