Water → (S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamic acid

HRID 1588473

Reaktionsgleichung

Reaktionsgleichung von HRID 1588473
[C:1]([S:5]([CH2:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([O:12]CC)=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+]>CS(C)=O.[OH-].[Ca+2].[OH-]>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]([OH:12])=[O:11])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14158057ethyl (RS)-alpha-[(tert-butylsulfonyl)methyl]hydrocinnamate

Produkt 1

HCID 9860623(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamic acidAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6093208Calcium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 79 g (0.25 mol) of ethyl (RS)-α-[(tert-butylsulfonyl)methyl]hydrocinnamate in 105 ml of dimethyl sulfoxide was added dropwise while stirring vigorously to 6.2 l of water at 30° C. The pH value was adjusted to 7.5 with 0.1N sodium hydroxide solution. The hydrolysis was started by the addition of 1.05 g of α-chymotrypsin. The pH value was held constant at 7.5 using automatic titration by dosing-in 0.043N calcium hydroxide solution of 30° C. After a consumption of 2.67 l of 0.043N calcium hydroxide solution (after 19.5 hours), the reaction mixture was extracted three times with 2 l of ethyl acetate. The aqueous phase was acidified to pH 2.5 with 5% hydrochloric acid and extracted twice with 2 l of ethyl acetate. The organic phases were filtered over DICALITE Speedex, combined and dried over magnesium sulfate. After evaporating the solvent and drying the residue in a high vacuum, there were obtained 35 g (0.12 mol, 48.3%, 96.9% of theory) of (S)-α-[(tert-butylsulfonyl)methyl]hydrocinnamic acid in the form of white crystals, which had an enantiomeric excess of >98%. In order to determine the purity by gas chromatography, the compound obtained was silylated and had a purity of >99%.

Aufarbeitung

  1. additionThe hydrolysis was started by the addition of 1.05 g of α-chymotrypsin
  2. customAfter a consumption of 2.67 l of 0.043N calcium hydroxide solution (after 19.5 hours)
  3. extractionthe reaction mixture was extracted three times with 2 l of ethyl acetate
  4. extractionextracted twice with 2 l of ethyl acetate
  5. filtrationThe organic phases were filtered over DICALITE Speedex
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporating the solvent
  8. customdrying the residue in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-18dfd0bd20144a6faca4a01a8895fdb3
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223432

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