Trifluoroacetic acid → HCID 14690685, compound

HRID 629798Notes

Reaction equation

HRID 629798 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:9](C(OC(C)(C)C)=O)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726413HCID 86726413, compound

Product 1

HCID 14690685HCID 14690685, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl (2,5-difluorophenyl)imidodicarbonate (1.48 g, 4.49 mmol) was dissolved in DCM (15.0 mL) at rt. TFA (0.48 mL, 6.28 mmol) was added to the reaction and the contents were stirred for 1 h. LC/MS at this time shows that starting material has been consumed. The solution was then washed with saturated aqueous sodium bicarbonate. The organics were dried over MgSO4 filtered and concentrated. The crude product was purified on silica gel, eluting with 0-50% EtOAc in hexanes over 32 minutes to afford the title compound (758 mg, 2.88 mmol) as a pale yellow oil. MS (ESI): m/z=174.2 (M+H-[t-Bu]).

Workup

  1. customhas been consumed
  2. washThe solution was then washed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified on silica gel
  7. washeluting with 0-50% EtOAc in hexanes over 32 minutes

Sources & evidence

ORD record
ord-13223af647d4441084997daaa56da1cd
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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