Trifluoroacetic acid → HCID 69797124, compound

HRID 1063419Notes

Reaction equation

HRID 1063419 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12](=[O:20])[O:11][CH2:10]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][CH:9]1[CH2:10][O:11][C:12](=[O:20])[CH:13]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69797413HCID 69797413, compound

Product 1

HCID 69797124HCID 69797124, compoundYield 151.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5-Oxo-4-phenyl-tetrahydrofuran-3-ylmethyl)carbamic acid tert-butyl ester (Description 4; 2.16 g, 7.4 mmol) was dissolved in dichloromethane (10 ml), cooled to 0° C., trifluoroacetic acid (1 ml) was added and the reaction was left to stand for 20 minutes to warm to room temperature. TLC showed the reaction to be incomplete so extra trifluoroacetic acid (1 ml) was added and the reaction was left for a further 30 minutes. The solvent was removed in vacuo and the residue was dispersed between ethyl acetate and saturate potassium carbonate solution. The aqueous layer was extracted with ethyl acetate (2×30 ml), the combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to dryness. Purification was carried out by flash column chromatography on silica gel eluting in increasing concentrations of methanol in dichloromethane and 0.2% ammonia (1-10%) to afford the title compound (2.15 g).

Workup

  1. waitthe reaction was left
  2. temperatureto warm to room temperature
  3. customthe reaction
  4. additionwas added
  5. waitthe reaction was left for a further 30 minutes
  6. customThe solvent was removed in vacuo
  7. additionthe residue was dispersed between ethyl acetate
  8. concentrationsaturate potassium carbonate solution
  9. extractionThe aqueous layer was extracted with ethyl acetate (2×30 ml)
  10. washthe combined organic layers were washed with brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customevaporated to dryness
  14. customPurification
  15. temperaturein increasing concentrations of methanol in dichloromethane and 0.2% ammonia (1-10%)

Sources & evidence

ORD record
ord-35d65d1934ac4b4198d47c3fdea9b5f0
Source dataset
uspto-grants-2005_11
Patent number
US06964981B2

Reaction notes

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