Hydrazine hydrate (1:1) → 2-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

HRID 914287

Reaktionsgleichung

Reaktionsgleichung von HRID 914287
[C:1]([O:5][C:6](=[O:29])[C:7]([CH3:28])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[N:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6](=[O:29])[C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][NH2:17])[N:14]=1)([CH3:28])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 597588282-Methyl-2-{[4-(2-phthalimidoethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester

Produkt 1

HCID 597594492-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl esterAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Methyl-2-{[4-(2-phthalimidoethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester (136 g) synthesized in Example 6 was dissolved in ethanol (800 mL), hydrazine monohydrate (47.2 g) was added, and the mixture was refluxed for 4 hr. White precipitate was filtered off from the reaction mixture, and the filtrate was concentrated under reduced pressure. Water was added thereto, and the mixture was extracted with dichloroethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (77.6 g) as a brown oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 hr
  2. filtrationWhite precipitate was filtered off from the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added
  5. extractionthe mixture was extracted with dichloroethane
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-667b6ffa27e946afb16f92fd2515a8f1
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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