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2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate

HRID 1266771
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1266771
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=O.C(C([O:22][CH2:23][C:24]([NH2:26])=[S:25])=O)(C)(C)C>CCO>[OH:22][CH2:23][C:24]1[S:25][C:2]([CH3:15])=[C:3]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])[N:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 27821132-Amino-2-thioxoethyl 2,2-dimethylpropanoateHCID 22139798Rac-3-(2-bromo-propionyl)-benzoic acid methyl ester

Produkt 1

HCID 18548740Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoateAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of methyl 3-(2-bromo-propionyl)-benzoate (2.7 g) and 2-(tert.-butyl-carbonyloxy)thioacetamide (2.1 g) in EtOH (20 mL) was heated at reflux for 8 h. The mixture was partitioned between H2O and AcOEt. The organic layer was dried and evaporated. The residue was dissolved in MeOH (20 ml), NaOMe (0.54 g) was added, and the mixture was heated to 60° C. for 1 h. The mixture was diluted with AcOEt and then washed with 3N HCl and brine. The organic layer was dried and evaporated and the residue was crystallized from AcOEt to give methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate (1.17 g) as white solid.

Aufarbeitung

  1. temperatureat reflux for 8 h
  2. customThe mixture was partitioned between H2O and AcOEt
  3. customThe organic layer was dried
  4. customevaporated
  5. dissolutionThe residue was dissolved in MeOH (20 ml)
  6. additionNaOMe (0.54 g) was added
  7. additionThe mixture was diluted with AcOEt
  8. washwashed with 3N HCl and brine
  9. customThe organic layer was dried
  10. customevaporated
  11. customthe residue was crystallized from AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-780c0c6dc70f4ae28f07998a4264b8ef
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06548495B2

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