Water → HCID 131736896, compound

HRID 56025Notes

Reaction equation

HRID 56025 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:20][OH:21])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:29]([CH3:31])[CH3:30].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:9](=[N:20][O:21][CH:29]([CH3:31])[CH3:30])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 137222800tert-butyl (S)-N-[2-(3,5-dichloropyridin-2-yl)-2-hydroxyimino-1-methylethyl]carbamate

Product 1

HCID 131736896HCID 131736896, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 655 mg of tert-butyl (S)—N-[2-(3,5-dichloropyridin-2-yl)-2-hydroxyimino-1-methylethyl]carbamate in 1.6 ml of N,N-dimethylformamide, 445 mg of potassium carbonate and 789 mg of 2-iodopropane were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 5 ml of water and extracted with ethyl acetate (10 ml×2), the resulting organic layers were combined, washed with water (10 ml×2) and dried over saturated aqueous sodium chloride and then aqueous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 0:10 to 3:7) as the eluent to obtain 411 mg of the desired product as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 ml×2)
  3. washwashed with water (10 ml×2)
  4. dry with materialdried over saturated aqueous sodium chloride
  5. customaqueous sodium sulfate, and the solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c06bbe7a246344fbbaaca3455ff54331
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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