Ethanol → HCID 66782861, Verbindung

HRID 1096295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096295
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@@H:14]([OH:18])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:24][CH2:25]O>>[CH2:24]([O:16][C:15](=[O:17])[C@H:14]([OH:18])[CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:25]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7004002(R)-4-(((Benzyloxy)carbonyl)amino)-2-hydroxybutanoic acid

Produkt 1

HCID 66782861HCID 66782861, VerbindungAusbeute 81 %

Versuchsvorschrift

A solution of (R)-4-benzyloxycarbonylamino-2-hydroxy-butyric acid (2.42 g, 9.56 mmol) and sulfuric acid (94 mg, 0.96 mmol) in EtOH (6 mL) was heated at reflux for 18 h, then partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound (2.18 g, 81%). Light yellow liquid, MS: 304.2 (M+Na)+.

Aufarbeitung

  1. temperatureat reflux for 18 h
  2. custompartitioned between EtOAc and sat. aq. NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8fc82388e0f34039811990c1957635ff
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138175B2

Notizen zur Reaktion

Wird geladen…