Reaction #48826

Reaction equation

Trimethylsilyl iodide

tert-butyl 3-({3-[4-(ethoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Sodium thiosulfate

→

oil

Yield 111.3%

Ethyl 4-{3-[(S)-2-hydroxy-1-methylethoxy]-5-[(1H-pyrazol-3-ylamino)carbonyl]phenoxy}benzoate

Yield 111.3%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherto quench
2. 2
   Otherthe reaction
3. 3
   Extractionthe reaction mixture was extracted into ethyl acetate (3×25 mL)
4. 4
   Dryingdried (MgSO4)
5. 5
   Concentrationthe filtrate was concentrated in vacuo

Procedure

Trimethylsilyl iodide (0.27 mL) was added dropwise under argon to a solution of tert-butyl 3-({3-[4-(ethoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (167 mg, 0.38 mmol) in acetonitrile (5 mL) and stirred at ambient temperature for 16 hours. Sodium thiosulfate solution was added to quench the reaction and the reaction mixture was extracted into ethyl acetate (3×25 mL). Organic phases were combined and dried (MgSO4) and the filtrate was concentrated in vacuo to give a clear oil (180 mg), which was not purified further.

Source