Hydrochloric Acid → HCID 54107311, compound

HRID 369739Notes

Reaction equation

HRID 369739 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]([NH:21]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:19][CH:20]=1)[C:5]([OH:17])([C:10]#[C:11][C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[C:6]([F:9])([F:8])[F:7].Cl.C(=O)(O)[O-].CCOCC>CO>[NH2:21][C:18]1[C:4]([C:5]([OH:17])([C:10]#[C:11][C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:6]([F:7])([F:8])[F:9])=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 3283Diethyl EtherHCID 15486989HCID 15486989, compound

Product 1

HCID 54107311HCID 54107311, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 20 g of 3-Chloro-6-(triphenylmethy)amino-α-(2-furanyl)ethynyl-α-(trifluoromethyl)benzyl alcohol (Example 9, Part B) in 20 mL of methanol was added 0.125 mL of 12 N aqueous hydrochloric acid, and the resulting solution was stirred at ambient temperature for 30 min. The reaction mixture was poured onto aqueous bicarbonate and extractec with ether. The ether layer was washed with brine, dried and evaporated. The residue was dissolved in methanol after cooling in ice for 1 h, the precipitated methyl trityl ether was filtered off. After evaporation of the filtrate, the residue was chromatographed over silica gel (elution with hexanes/ethyl acetate 3:1) affording after crystalization from hexane/ethyl acetate 280 mg of the title compound.

Workup

  1. washThe ether layer was washed with brine
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in methanol
  5. temperatureafter cooling in ice for 1 h
  6. filtrationthe precipitated methyl trityl ether was filtered off
  7. customAfter evaporation of the filtrate
  8. customthe residue was chromatographed over silica gel (elution with hexanes/ethyl acetate 3:1)
  9. customaffording
  10. customafter crystalization from hexane/ethyl acetate 280 mg of the title compound

Sources & evidence

ORD record
ord-b10218ad5bc9474cb94dc682ae3760b2
Source dataset
uspto-grants-2000_10
Patent number
US06140320

Reaction notes

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