Reaktion #2444256

Reaktionsgleichung

(R)-3-(tert-butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid

(R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid

HATU

DIPEA

4-(octylthio)-3-(trifluoromethyl)benzohydrazide

4-(Octylthio)-3-(trifluoromethyl)benzohydrazide

NaHCO3

→

(R)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octylthio)-3-(trifluoromethyl)benzoyl)hydrazinecarbonyl)oxazolidine-3-carboxylate

Ausbeute 84.0%

(R)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octylthio)-3-(trifluoromethyl)benzoyl)hydrazine carbonyl)oxazolidine-3-carboxylate

Ausbeute 84.0%

Lösungsmittel

DMF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas left
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Extraktionthe mixture was extracted with EtOAc
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   Sonstigeto give a residue, which
8. 8
   Sonstigewas purified by SiO2 column chromatograph (n-hexane/EtOAc=3:7)

Vorschrift

To a solution of (R)-3-(tert-butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid 4 (129.6 mg, 0.5 mmol) in DMF (1 mL) was added HATU (209 mg, 0.55 mol) and DIPEA (0.436 mL, 2.5 mmol). After being stirred at rt for 10 min, the reaction mixture was treated with 4-(octylthio)-3-(trifluoromethyl)benzohydrazide 3a (174 mg, 0.5 mmol) in THF (2 mL) and was left stirred overnight. Aqueous NaHCO3 solution was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure to give a residue, which was purified by SiO2 column chromatograph (n-hexane/EtOAc=3:7) to give (R)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octylthio)-3-(trifluoromethyl)benzoyl)hydrazinecarbonyl)oxazolidine-3-carboxylate 5a (247 mg, 84%). HPLC retention time on a C18 column (30×4.6 mm, 3.5μ) was 3.08 min with gradient 10-95% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase. MS (ESI, M+H+)=590.5

Quelle