反応 #48826

ord-41f61ad5ddc44ea48222b7de70689e06

反応方程式

C[Si](C)(C)I
Trimethylsilyl iodide
CCOC(=O)c1ccc(Oc2cc(O[C@@H](C)COC)cc(C(=O)Nc3ccn(C(=O)OC(C)(C)C)n3)c2)cc1
tert-butyl 3-({3-[4-(ethoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate
O=S([O-])([O-])=S.[Na+].[Na+]
Sodium thiosulfate
CCOC(=O)c1ccc(Oc2cc(O[C@@H](C)CO)cc(C(=O)Nc3cc[nH]n3)c2)cc1
oil
収率 111.3%
CCOC(=O)c1ccc(Oc2cc(O[C@@H](C)CO)cc(C(=O)Nc3cc[nH]n3)c2)cc1
Ethyl 4-{3-[(S)-2-hydroxy-1-methylethoxy]-5-[(1H-pyrazol-3-ylamino)carbonyl]phenoxy}benzoate
収率 111.3%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他to quench
  2. 2
    その他the reaction
  3. 3
    抽出the reaction mixture was extracted into ethyl acetate (3×25 mL)
  4. 4
    乾燥dried (MgSO4)
  5. 5
    濃縮the filtrate was concentrated in vacuo

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07745475B2uspto-grants-2010_06