tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 57214691, compound

HRID 1487129Notes

Reaction equation

HRID 1487129 reaction equation
C([NH:5][C:6](=[O:18])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:8])(C)(C)C.FC(F)(F)S(O[Si](C(C)(C)C)(C)C)(=O)=O>C1(C)C=CC=CC=1>[N+:15]([C:11]1[CH:10]=[C:9]([C:7](=[O:8])[C:6]([NH2:5])=[O:18])[CH:14]=[CH:13][CH:12]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 23336273HCID 23336273, compound

Product 1

HCID 57214691HCID 57214691, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen atmosphere, (tert-butyl)-2-(3-nitrophenyl)-2-oxoacetamide (1.50 g, 5.99 mmol) was taken in toluene (10 ml) at room temperature, tert-butyldimethylsilyl trifluoromethane sulfonate (1.378 ml, 5.99 mmol) was added and the reaction mixture was heated at 100° C. for 8 hrs. The reaction mixture was concentrated under vacuum and satd. sodium bicarbonate solution was added, the mixture was extracted with ethyl acetate (3×20 ml). Combined organic layer was dried over sodium sulfate and the mixture was concentrated under vacuum to afford the crude product, which was purified by column chromatography to afford yellow solid product (440 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionsodium bicarbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate (3×20 ml)
  4. dry with materialCombined organic layer was dried over sodium sulfate
  5. concentrationthe mixture was concentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-012034268fdb4980b11d96f1742ec650
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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