Trifluoroacetic acid → HCID 67126832, compound

HRID 2045107Notes

Reaction equation

HRID 2045107 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:21]([N:24](CC2C=CC(OC)=CC=2OC)CC2C=CC(OC)=CC=2OC)(=[O:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1([F:20])[CH2:15][CH2:14][N:13]([CH:16]2[CH2:19][O:18][CH2:17]2)[CH2:12][CH2:11]1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:21]([NH2:24])(=[O:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1([F:20])[CH2:11][CH2:12][N:13]([CH:16]2[CH2:17][O:18][CH2:19]2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67227347HCID 67227347, compound

Product 1

HCID 67126832HCID 67126832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 517D (0.258 g) in dichloromethane (3 mL) was added trifluoroacetic acid (2 mL) dropwise. The reaction was stirred for 1 hour then quenched by the addition of saturated NaHCO3 solution (20 mL). The reaction was extracted with dichloromethane (2×50 mL), the dichloromethane layer was concentrated, ethyl acetate (20 mL) was added and the resulting solid was filtered. The organic layer was diluted to 50 ml, washed with brine (25 mL), dried over magnesium sulfate, filtered and concentrated. The resulting oil was treated with dichloromethane and concentrated, and the solid was triturated with ethyl acetate and filtered to give the title compound.

Workup

  1. customthen quenched by the addition of saturated NaHCO3 solution (20 mL)
  2. extractionThe reaction was extracted with dichloromethane (2×50 mL)
  3. concentrationthe dichloromethane layer was concentrated
  4. additionethyl acetate (20 mL) was added
  5. filtrationthe resulting solid was filtered
  6. additionThe organic layer was diluted to 50 ml
  7. washwashed with brine (25 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. additionThe resulting oil was treated with dichloromethane
  12. concentrationconcentrated
  13. customthe solid was triturated with ethyl acetate
  14. filtrationfiltered

Sources & evidence

ORD record
ord-0d87258611404523852b8573cd5e9ac9
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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