Acetic Acid → HCID 87294675, Verbindung

HRID 872658

Reaktionsgleichung

Reaktionsgleichung von HRID 872658
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[OH:11][CH:12]([CH3:16])[C:13](=O)[CH3:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[OH:11][CH:12]([CH3:16])[CH:13]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1)[CH3:14]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 179AcetoinHCID 516892Sodium BicarbonateHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 5049666Sodium triacetoxyborohydride2×

Produkt 1

HCID 87294675HCID 87294675, VerbindungAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Methyl 2-aminothiazole-4-carboxylate (1.0, 6.32 mmol), 3-hydroxy-2-butanone (1.045 ml, 12.01 mmol) and acetic acid (2.278 g, 37.9 mmol) were dissolved in 1,2-dichloroethane. Sodium triacetoxy borohydride (3.75 g, 17.70 mmol) was added and the reaction mixture was stirred overnight. Sodium triacetoxy borohydride (3.1 g) was added in two portions and the reaction mixture was stirred over two nights. 1M NaHCO3 was added slowly and mixture was extracted twice with DCM. DCM phase was dried and evaporated to afford 68.1% of the title product. m/z [230.3+1].

Aufarbeitung

  1. stirringthe reaction mixture was stirred over two nights
  2. extractionmixture was extracted twice with DCM
  3. dry with materialDCM phase was dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a6bd3f90f4be4c78ba629aeef51036c1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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