Trifluoroacetic acid → HCID 69016002, compound

HRID 491586Notes

Reaction equation

HRID 491586 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:25]([F:28])([F:27])[F:26])=[C:9]([CH:24]=1)[O:10][CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[NH:13]1[CH2:14][CH2:15][CH2:16][C@@H:12]1[CH2:11][O:10][C:9]1[CH:24]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[C:25]([F:28])([F:27])[F:26]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69016186HCID 69016186, compound

Product 1

HCID 69016002HCID 69016002, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (R)-2-(5-acetylamino-2-trifluoromethyl-phenoxymethyl)-1-(tert-butoxycarbonyl)pyrrolidine (1.34 g, 3.33 mol) in 10 mL CH2Cl2 at RT was added 5 mL TFA. The reaction was stirred for 50 min, neutralized with saturated aqueous NaHCO3, and diluted with CH2Cl2 and 2N NaOH. The layers were separated, and the organic layer was brine-washed. The aqueous layers were back-extracted 4 times with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to yield the title compound.

Workup

  1. customThe layers were separated
  2. washwashed
  3. extractionThe aqueous layers were back-extracted 4 times with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2837b5499d44f198c46054ad49aaa38
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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