Trifluoroacetic acid → HCID 22730527, compound

HRID 1785749Notes

Reaction equation

HRID 1785749 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-dd36ffd6275a4c4189df4bd2097db1f6
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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