Sulfuric Acid → Acetic acid, [(1-methylethyl)thio][[(phenylmethoxy)carbonyl]amino]-

HRID 1080376

Reaktionsgleichung

Reaktionsgleichung von HRID 1080376
O[CH:2]([C:14]([OH:16])=[O:15])[NH:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH:17]([SH:20])([CH3:19])[CH3:18].OS(O)(=O)=O>C(O)(=O)C>[CH:17]([S:20][CH:2]([C:14]([OH:16])=[O:15])[NH:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 63642-PropanethiolHCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

Produkt 1

HCID 11346620Acetic acid, [(1-methylethyl)thio][[(phenylmethoxy)carbonyl]amino]-Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

α-hydroxy-N-benzyloxycarbonylglycine 22A (5.57 g, 0.027 mol) of Example 1 was stirred with isopropylmercaptan (8.29 g, 0.11 mol) in glacial acetic acid (26.5 mL) at 0° C. Conc H2SO4 (0.27 mL) was added and the mixture stirred for 2 days at room temperature. The mixture was then poured into ice and the organic layer extracted with ethyl acetate. The ethyl acetate solution was washed with water, 5% NaHCO3, dried over MgSO4, solvent removed to give 22B in 94% yield. This was used without further purification.

Aufarbeitung

  1. additionThe mixture was then poured into ice
  2. extractionthe organic layer extracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with water, 5% NaHCO3
  4. dry with materialdried over MgSO4, solvent
  5. customremoved

Quellen und Nachweise

ORD-Eintrag
ord-b3b359cee4614acc9ed20aa7c9d88e9e
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580979

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