Trifluoroacetic acid → HCID 65245104, compound

HRID 403302Notes

Reaction equation

HRID 403302 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:11][CH:10]([NH:12]C(=O)OC(C)(C)C)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:12][CH:10]1[CH2:11][N:8]([C:6]([C:5]2[CH:20]=[CH:21][C:2]([Br:1])=[CH:3][CH:4]=2)=[O:7])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67473789HCID 67473789, compound

Product 1

HCID 65245104HCID 65245104, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 16c (810 mg, 2.28 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (7 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The resulting mixture was concentrated. To the residue was added CH2Cl2 and 1N aqueous NaOH solution until the pH of the aqueous layer was approximately 8. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give compound 16d (570 mg). MS m/z (M+H+) 254, 256.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additionTo the residue was added CH2Cl2 and 1N aqueous NaOH solution until the pH of the aqueous layer
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa18c3f1622a4695b8bda4c4c973405c
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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