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

HRID 1487173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487173
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-110d67e3c77a4d46828757eda998cc6b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428508B2

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