Trifluoroacetic acid → HCID 57656455, compound

HRID 2041140Notes

Reaction equation

HRID 2041140 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:10]=1[F:22])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:22][C:10]1[CH:11]=[C:12]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=[CH:14][C:9]=1[CH2:8][NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66706560Carbamic acid, [(2-fluoro-4-phenoxyphenyl)methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 57656455HCID 57656455, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2-fluoro-4-phenoxy-benzyl)-carbamic acid tert-butyl ester (2.44 g, 7.72 mmol) in DCM (200 mL). Add trifluoroacetic acid (50 mL) then stir at ambient temperature for 16 h. Evaporate the solvent, dissolve the residue in DCM and wash with 1N aqueous NaOH. Dry over Na2SO4 and concentrate in vacuo. Purify by SCX chromatography to obtain the title compound (557 mg, 33%). MS (ES+) m/z: 201 (M+H—NH3)+.

Workup

  1. customEvaporate the solvent
  2. dissolutiondissolve the residue in DCM
  3. washwash with 1N aqueous NaOH
  4. dry with materialDry over Na2SO4
  5. concentrationconcentrate in vacuo
  6. customPurify by SCX chromatography

Sources & evidence

ORD record
ord-267a0fd8014a4e16905c54af9d79e9e8
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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