Trifluoroacetic acid → HCID 22730527, compound

HRID 2356000Notes

Reaction equation

HRID 2356000 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:21]N1C(C)(C)C(=O)N(Br)C1=O.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Br:21][C:13]1[CH:12]=[C:11]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:10]=[C:9]([N+:18]([O-:20])=[O:19])[C:8]=1[NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 516892Sodium BicarbonateHCID 22660807HCID 22660807, compound

Product 1

HCID 22730527HCID 22730527, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A room temperature solution of Example 3A (1.81 g, 6.0 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (950 mg, 3.3 mmol) in dichloromethane was treated with trifluoracetic acid (796 uL, 9.0 mmol), stirred in darkness for 18 hours, treated with saturated NaHCO3, and extracted with diethyl ether. The combined extracts were washed with brine, dried (Na2SO4), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 376 (M−H)−.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ba8861fc621b4459bf519028ef7942a2
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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