Sodium Thiosulfate → HCID 178469074, compound

HRID 20548Notes

Reaction equation

HRID 20548 reaction equation
C[Si](I)(C)C.[CH2:6]([O:8][C:9]([C:11]1[CH:44]=[CH:43][C:14]([O:15][C:16]2[CH:17]=[C:18]([CH:34]=[C:35]([O:37][C@@H:38]([CH3:42])[CH2:39][O:40]C)[CH:36]=2)[C:19]([NH:21][C:22]2[CH:26]=[CH:25][N:24](C(OC(C)(C)C)=O)[N:23]=2)=[O:20])=[CH:13][CH:12]=1)=[O:10])[CH3:7].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[OH:40][CH2:39][C@H:38]([CH3:42])[O:37][C:35]1[CH:36]=[C:16]([CH:17]=[C:18]([C:19]([NH:21][C:22]2[CH:26]=[CH:25][NH:24][N:23]=2)=[O:20])[CH:34]=1)[O:15][C:14]1[CH:13]=[CH:12][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 59346927HCID 59346927, compound

Product 1

HCID 178469074HCID 178469074, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted into ethyl acetate (3×25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-41f61ad5ddc44ea48222b7de70689e06
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

Loading…