Trifluoroacetic acid → HCID 18516365, compound

HRID 1369910Notes

Reaction equation

HRID 1369910 reaction equation
C(OC([N:8]1[C:17]2[C:16]([F:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH:11]2[CH2:19][CH2:20][CH2:21][C:10]2([F:22])[C:9]1=[O:23])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O.C(OCC)(=O)C>[F:22][C:10]12[CH2:21][CH2:20][CH2:19][CH:11]1[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:18])[C:17]=1[NH:8][C:9]2=[O:23]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18516387HCID 18516387, compound

Product 1

HCID 18516365HCID 18516365, compoundYield 44.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 200 mg (0.6 mmol) of 5-tert-butoxycarbonyl-3a,6-difluoro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 2 ml of dichloromethane is mixed with 2 ml of trifluoroacetic acid at room temperature. After 30 minutes, the batch is diluted with water and ethyl acetate. The organic phase is separated, washed with water, saturated NaHCO3 and saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography of the residue on silica gel with hexane-ethyl acetate yields 60 mg of product.

Workup

  1. customThe organic phase is separated
  2. washwashed with water, saturated NaHCO3 and saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-fb22059c69fa488791e114695be11229
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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