Water → HCID 14672237, Verbindung

HRID 850364

Reaktionsgleichung

Reaktionsgleichung von HRID 850364
[NH:1]1[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].O.[C:10]1([CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[OH-].[Na+].C1C=CC=CC=1>[C:10]1([CH2:16][CH2:17][CH2:18][C:19]([N:1]2[CH2:8][S:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])=[O:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 93176L-ThioprolineHCID 117898654-Phenylbutanoyl Chloride

Produkt 1

HCID 14672237HCID 14672237, VerbindungAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

Dissolved in 100 ml of 1N sodium hydroxide were 6.65 g of L-thioproline, and 50 ml of water were further added to the solution. A solution of 9.10 g of 4-phenylbutanoyl chloride in 50 ml of benzene was added dropwise to the solution under stirring. Thereafter, 50 ml of 1N sodium hydroxide were further added, and the mixture was stirred for 24 hours. A benzene layer was removed, and a water layer was washed twice with 70 ml of ether. After 7% hydrochloric acid was further added to the water layer to acidify it, the water layer was extracted three times with 70 ml of ethyl acetate. The resulting extract was dried over anhydrous sodium sulfate. Ethyl acetate was distilled off, and the resultant oily residue was subjected to column chromatography on silica gel, thereby obtaining 11.4 g of N-(4-phenylbutanoyl)-L-thioproline as colorless crystals from a chloroform-methanol fraction.

Aufarbeitung

  1. additionwere further added to the solution
  2. stirringthe mixture was stirred for 24 hours
  3. customA benzene layer was removed
  4. washa water layer was washed twice with 70 ml of ether
  5. additionAfter 7% hydrochloric acid was further added to the water layer
  6. extractionthe water layer was extracted three times with 70 ml of ethyl acetate
  7. extractionThe resulting extract
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. distillationEthyl acetate was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-c034709671e1431884838a614ad779c8
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017929

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