Trifluoroacetic acid → HCID 53774617, compound

HRID 2255270Notes

Reaction equation

HRID 2255270 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:17]3[C:12]([CH3:23])([C:13]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:14]=4[CH2:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:24])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C@@H:17]3[C@:12]([CH3:23])([C:13]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10][C:9]2=[O:24])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19707310HCID 19707310, compound

Product 1

HCID 53774617HCID 53774617, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of subtitle compound from Step B (693 mg) in CH2Cl2 (2.5mL) under a nitrogen atmosphere was added triethylsilane (1.4 ml) The reaction mixture was stirred for 15 minutes. To the solution was added 1.5 mL of trifluoroacetic acid and the reaction mixture stirred at room temperature overnight. The reaction mixture was partitioned between CHCl3 and saturated NaHCO3. The organic phase was dried over Na2SO4 and the solvent removed under vacuum. The residue was purified by chromatography on SiO2 (25% ethyl acetate in hexanes as eluent). The product containing fractions were evaporated under vacuum to afford 459 mg of the subtitle compound as a foam. Melting point 55°-60° C.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. customThe reaction mixture was partitioned between CHCl3 and saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent removed under vacuum
  5. customThe residue was purified by chromatography on SiO2 (25% ethyl acetate in hexanes as eluent)
  6. additionThe product containing fractions
  7. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-01d35965e01f48b3b4c851466dd30eca
Source dataset
uspto-grants-1993_08
Patent number
US05239075

Reaction notes

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