Trifluoroacetic acid → HCID 59323300, compound

HRID 2390036Notes

Reaction equation

HRID 2390036 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[CH2:17][C:18](=O)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.[BH4-].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)C>[CH2:19]([CH:18]1[CH2:17][C:11]2[C:10](=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:16])[CH2:9][NH:8]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59323461HCID 59323461, compound

Product 1

HCID 59323300HCID 59323300, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

427 mg of 1-[2-(tert-butoxycarbonylaminomethyl)-6-chlorophenyl]-3-phenyl-2-propanone was dissolved in 5 mL of methylene chloride, and 3 mL of trifluoroacetic acid was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. After confirming the loss of the starting material, it was concentrated under reduced pressure, and the residue obtained was dissolved in 5 mL of ethanol. 173 mg of sodium borohydride was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was recrystallized using chloroform hexane to obtain 173 mg of a title compound as a white crystal. Further, a mother liquor upon recrystallization operation was purified using PLC (chloroform:methanol=20:1) to obtain 88.6 mg of a title compound as a pale yellow oily substance. In total, 262 mg (yield 89%) of a title compound was obtained.

Workup

  1. temperatureunder ice-cooling
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue obtained
  4. temperatureunder ice-cooling
  5. stirringby stirring at room temperature for 1 hour
  6. customAfter completion of the reaction
  7. extractionfollowed by extraction with chloroform
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue obtained
  12. customwas recrystallized

Sources & evidence

ORD record
ord-d7b51e1d1f8b47c585678a39e4400152
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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