4-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester → 4-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

HRID 248079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248079
[CH3:1][C:2]([CH3:22])([O:4][C:5](=[O:21])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])=[CH:10][CH:9]=1)[CH3:3]>C(OCC)C.P([O-])([O-])([O-])=O>[CH3:22][C:2]([CH3:3])([O:4][C:5](=[O:21])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:20])[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1)[CH3:1]

Komponenten

4

Edukt 1

HCID 867467874-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester

Produkt 1

HCID 197645314-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1061PhosphateLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Dissolve (+)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester (5.74 g, 18.6 mmol) in ethyl ether and adsorb onto silica gel (18 g). Evaporate the solvent in vacuo to leave a white powder. Suspend the powder in pH 7 phosphate buffer (600 mL of a 0.1M solution). Add lipase P-30 (5.74 g) and stir for 16 hours. Filter and extract with ethyl ether (3×400 mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by flash chromatography (5→10% methanol/chloroform) to give the title compound (5.09 g, 98% ee after reesterification with diazomethane); [α]d 20 =+18.9° (C=0.97, CHCl3).

Aufarbeitung

  1. customEvaporate the solvent in vacuo
  2. customto leave a white powder
  3. additionAdd lipase P-30 (5.74 g)
  4. filtrationFilter
  5. extractionextract with ethyl ether (3×400 mL)
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. custompurify by flash chromatography (5→10% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-0a447fe48068438388e9bd6053bd951f
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208240

Notizen zur Reaktion

Wird geladen…