반응 #88933

반응 방정식

NaOH

Intermediate 61c

[5-(5-Amino-3-tert-butyl-pyrazol-1-yl)-2-triisopropylsilanyloxy-phenyl]-methanol

NaOH

2,2,2-trichloroethylchloroformate

2,2,2-trichloroethylchloroformate

→

title compound

수율 84.0%

[5-tert-Butyl-2-(3-hydroxymethyl-4-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

수율 84.0%

용매

EtOAc

EtOAc

water

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring for another 4 h
2. 2
   추출The aqueous layer was then extracted with EtOAc (2×)
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   기타evaporated in vacuo
7. 7
   기타The residue was purified by FCC

실험 절차

To a solution of Intermediate 61c (0.15 g, 0.36 mmol) in EtOAc (1.8 mL) was added 1N aqueous NaOH solution (0.6 mL, 0.60 mmol) followed by 2,2,2-trichloroethylchloroformate (54.0 μL, 0.40 mmol). The reaction was stirred at RT overnight then treated with another portion of 1N aqueous NaOH solution (0.3 mL, 0.30 mmol) followed by 2,2,2-trichloroethylchloroformate (27.0 μL, 0.20 mmol). After stirring for another 4 h, the mixture was diluted with EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-25% EtOAc in cyclohexane, to give the title compound (176 mg, 84%). LCMS (Method 3): Rt 5.35 min, m/z 592, 594 [MH+].

출처