Trifluoroacetic acid → HCID 70800861, compound

HRID 1754248Notes

Reaction equation

HRID 1754248 reaction equation
[C:1]1([C:7]2[CH:34]=[CH:33][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][NH:21][S:22]([NH:25]C(=O)OC(C)(C)C)(=[O:24])=[O:23])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[CH:34]=[CH:33][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][NH:21][S:22](=[O:23])(=[O:24])[NH2:25])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70800909HCID 70800909, compound

Product 1

HCID 70800861HCID 70800861, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 24a (1.16 g, 2.30 mmol) in DCM (10 mL) was added TFA (5 mL) and the reaction mixture stirred for 0.5 h. The reaction mixture was concentrated under reduced pressure then azeotroped from toluene (2×). The crude residue was diluted with 1.5M K3PO4 then the aqueous layer extracted with DCM (3×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified on silica gel eluting with 0-15% MeOH/DCM to give Compound 24b (68 mg, 74% yield) as a pale brown solid. LCMS=1.71 min using analytical method (B), 402.0 (M+H). 1H NMR (400 MHz, CD3OD) δ 8.24 (d, J=1.5 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.79 (dd, J=8.5, 1.8 Hz, 1H), 7.73-7.65 (m, 2H), 7.47 (t, J=7.7 Hz, 2H), 7.41-7.32 (m, 1H), 4.47 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthen azeotroped from toluene (2×)
  3. additionThe crude residue was diluted with 1.5M K3PO4
  4. extractionthe aqueous layer extracted with DCM (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified on silica gel eluting with 0-15% MeOH/DCM

Sources & evidence

ORD record
ord-bb4b796ca83047da863fdb21137c7521
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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