Ammonia → Benzyl rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate

HRID 275596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275596
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:29]>O1CCCC1.C(OCC)(=O)C>[C:17]([C:16]([S:13]([CH2:12][CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])(=[O:15])=[O:14])([CH3:21])[CH3:20])(=[O:18])[NH2:29]

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

Produkt 1

HCID 54066967Benzyl rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamateAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1.05 g (2.5 mmol) of crude (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride in 29 ml (9.3 mmol) of 0.32M ammonia in tetrahydrofuran was stirred at room temperature for 5 hours. Subsequently, the reaction solution was diluted with 40 ml of ethyl acetate and extracted with 20 ml of 1N hydrochloric acid. The ethyl acetate extract was then washed with 20 ml of saturated sodium hydrogen carbonate solution and 20 ml of saturated sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. There was obtained 0.92 g of benzyl rac-α-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate as a colourless solid, MS: 312 (M-benzyl)+.

Aufarbeitung

  1. extractionextracted with 20 ml of 1N hydrochloric acid
  2. extractionThe ethyl acetate extract
  3. washwas then washed with 20 ml of saturated sodium hydrogen carbonate solution and 20 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b20e8a71151b418ba7255c812bf9299e
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393875

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