Ethyl 2-(cyclopentanecarboxamido)-3-mercaptopropanoate → Ethyl 2-cyclopentyl-4,5-dihydrothiazole-4-carboxylate

HRID 446411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446411
[CH:1]1([C:6]([NH:8][CH:9]([CH2:15][SH:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1>[CH:1]1([C:6]2[S:16][CH2:15][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

3

Edukt 1

HCID 57989260Ethyl 2-(cyclopentanecarboxamido)-3-mercaptopropanoate

Produkt 1

HCID 57989100Ethyl 2-cyclopentyl-4,5-dihydrothiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tosic acid monohydrate (0.78 g) was added to a solution of ethyl 2-(cyclopentanecarboxamido)-3-mercaptopropanoate [Carboxylic Acid 2, step a] (5 g) in toluene (40 mL). The resulting mixture was heated at reflux under Dean and Stark conditions for 6 h. The reaction was allowed to cool, then the toluene solution was washed with saturated sodium bicarbonate solution (20 mL) and the solvent evaporated. The residue was azeotroped with toluene. The resulting white solid was purified by silica gel chromatography eluting with 9:1 isohexane:ethyl acetate. The fractions containing the product were combined and evaporated to give the subtitled compound as a clear oil. Yield 3.2 g.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under Dean and Stark conditions for 6 h
  3. temperatureto cool
  4. washthe toluene solution was washed with saturated sodium bicarbonate solution (20 mL)
  5. customthe solvent evaporated
  6. customThe residue was azeotroped with toluene
  7. customThe resulting white solid was purified by silica gel chromatography
  8. washeluting with 9:1 isohexane
  9. additionThe fractions containing the product
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d73df788d1db470dbe46f704e87ec044
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476265B2

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