Trifluoroacetic acid → HCID 67608196, compound

HRID 1965210Notes

Reaction equation

HRID 1965210 reaction equation
C(OC([N:8]1[CH:15]2[CH:11]([N:12]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[CH2:13][CH:14]2[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:29]([O:28][C:26]([N:12]1[CH2:13][CH:14]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH:15]2[NH:8][CH2:9][CH2:10][CH:11]12)=[O:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67608705HCID 67608705, compound

Product 1

HCID 67608196HCID 67608196, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of phenol-ether 78 (0.86 g, 1.8 mmol) in DCM (10 mL) was treated with TFA (3 mL) at 0° C. After 20 min, the reaction was warmed to ambient temperature. After 1 h, the solution was concentrated, diluted with EtOAc, washed successively with saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The aqueous phase was back-extracted with DCM and the combined organic extracts were concentrated to give amine 80 as an orange-colored oil that was used without further purification. Mass spectrum, m/z [389.5] (M+H)+.

Workup

  1. waitAfter 1 h
  2. concentrationthe solution was concentrated
  3. additiondiluted with EtOAc
  4. washwashed successively with saturated aqueous NaHCO3, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionThe aqueous phase was back-extracted with DCM
  9. concentrationthe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-cd50767aa9844c03bd3e9e7db00ddc82
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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