Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate → Ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate

HRID 524412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524412
C(OC([N:8](CC1C=CC(OC)=CC=1)[C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:20][CH:21]([CH3:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:20][CH:21]([CH3:22])[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1

Komponenten

3

Edukt 1

HCID 68182441Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate

Produkt 1

HCID 86669546Ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate (0.55 g, 1.2 mmol) was dissolved in TFA (7 mL). The reaction mixture was refluxed for 5 hours. TFA was removed under reduced pressure. The residue was diluted with water (10 mL) and ethyl acetate (15 mL) and basified with sodium bicarbonate. The organic layer was separated and aqueous layer was again extracted with ethyl acetate (15 mL). The combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to obtain crude product which was purified by silica gel column chromatography using 20% ethyl acetate in hexane to provide ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate (0.22 g).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customTFA was removed under reduced pressure
  3. additionThe residue was diluted with water (10 mL) and ethyl acetate (15 mL)
  4. customThe organic layer was separated
  5. extractionaqueous layer was again extracted with ethyl acetate (15 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude product which
  10. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b13024cc75f94df3a5a9b41b2a08af00
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340506B2

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