Trifluoroacetic acid → HCID 67078130, compound

HRID 1475648Notes

Reaction equation

HRID 1475648 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:7]([O:9]C(C)(C)C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68170292HCID 68170292, compound

Product 1

HCID 67078130HCID 67078130, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.20 g (about 88% pure, 6.96 mmol) of (+/−)-tert-butyl cyclopentyl(4-fluorophenyl)acetate were dissolved in 2.9 ml of dichloromethane, and 10.7 ml of trifluoroacetic acid were added at RT. The mixture was stirred at RT for 3 h and then concentrated under reduced pressure. The residue was dried under high vacuum overnight. The solid obtained was triturated with acetonitrile and then filtered off with suction and washed with a little acetonitrile. Drying under high vacuum gave 720 mg of a first solids batch. The filtrate obtained above was concentrated and the residue was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave a further 529 mg of the target product (overall yield 80.8% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was dried under high vacuum overnight
  3. customThe solid obtained
  4. customwas triturated with acetonitrile
  5. filtrationfiltered off with suction
  6. washwashed with a little acetonitrile
  7. customDrying under high vacuum

Sources & evidence

ORD record
ord-eab05b663895440e8afb02dda480e6f6
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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