Trifluoroacetic acid → HCID 18516353, compound

HRID 1369915Notes

Reaction equation

HRID 1369915 reaction equation
C(OC([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([Cl:18])=[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>[Cl:18][C:14]1[CH:15]=[CH:16][C:17]2[NH:8][C:9](=[O:23])[C:10]3([F:22])[CH2:21][CH2:20][CH2:19][CH:11]3[C:12]=2[CH:13]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18516358HCID 18516358, compound

Product 1

HCID 18516353HCID 18516353, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.20 g (6.5 mmol) of 5-tert-butoxycarbonyl-8-chloro-3a-fluoro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 10 ml of dichloromethane is mixed with 10 ml of trifluoroacetic acid at room temperature. After 2 hours, 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 0.83 g 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-b4d39e86b4d24e8d9d60a95be21f43f1
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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