Acetic Acid → HCID 178421671, compound

HRID 538366Notes

Reaction equation

HRID 538366 reaction equation
[F-].[K+].[Br:3][C:4]1[N:9]=[C:8]([C:10]2([CH3:25])[CH2:12][N@@:11]2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:7]([F:26])=[C:6]([Si](CC)(CC)CC)[CH:5]=1.CC(O)=O.C([O-])(O)=O.[Na+]>C1COCC1.CC(OC)(C)C.CN(C=O)C>[Br:3][C:4]1[N:9]=[C:8]([C:10]2([CH3:25])[CH2:12][N@@:11]2[S:13]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)(=[O:14])=[O:15])[C:7]([F:26])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 178477537HCID 178477537, compound

Product 1

HCID 178421671HCID 178421671, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Potassium fluoride (1.1 g, 18.85 mmol) was added to a solution of 6-bromo-3-fluoro-2-[(S)-2-methyl-1-(4-nitro-benzenesulfonyl)-aziridin-2-yl]-4-triethylsilanyl-pyridine (5 g, 9.43 mmol) and AcOH (1.13 g, 9.43 mmol) in 25 ml THF. DMF (35 ml) was added and the suspension was stirred for 1 h at rt. The reaction mixture was poured onto a mixture of sat. aq. NaHCO3 and TBME. The layers were separated and washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O, filtered and evaporated to give a yellow oil which was crystallized from TBME/hexane to yield 3.45 g of the title compound as white crystals.

Workup

  1. customThe layers were separated
  2. washwashed with brine and TBME
  3. dry with materialThe combined organic layers were dried over MgSO4.H2O
  4. filtrationfiltered
  5. customevaporated
  6. customto give a yellow oil which
  7. customwas crystallized from TBME/hexane

Sources & evidence

ORD record
ord-5675b3efb31f446998660ed260f5ed5f
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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