Trifluoroacetic acid → 1632310-24-7

HRID 1484409Notes

Reaction equation

HRID 1484409 reaction equation
[F:1][CH:2]([F:30])[C:3]([N:5]1[C@@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[NH:26])=[O:25])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7]C1(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:30][CH:2]([F:1])[C:3]([NH:5][C@H:9]([CH2:10][F:11])[C@H:8]([OH:7])[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[NH:26])=[O:25])=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117655310HCID 117655310, compound

Product 1

HCID 863006981632310-24-7Yield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2-difluoro-1-((4R,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(6-(methylsulfonimidoyl)pyridin-3-yl)phenyl)oxazolidin-3-yl)ethanone (250 mg, 0.567 mmol) in DCM (8 mL) is added TFA (1 mL) at 0° C. The reaction mixture is allowed to stir at room temperature for 4 h. Volatiles are removed under reduced pressure and crude is diluted using aqueous sodium bicarbonate and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by silica gel column chromatography (100-200 mesh size) using 8% methanol in DCM as an eluent to afford the title compound (170 mg) as a brown solid. 1NMR (400 MHz, DMSO) δ: 3.19 (d, 3H, J=0.76 Hz), 4.32-4.37 (m, 1.5H), 4.42-4.46 (m, 0.5H), 4.48 (bs, 1H), 4.53-4.56 (m, 0.5H), 4.66-4.69 (m, 0.5H), 4.91 (t, 1H), 5.97 (d, 1H, J=4.48 Hz), 6.20 (t, 1H, J=53.72 Hz), 7.51 (d, 2H, J=8.24 Hz), 7.79 (d, 2H, J=8.28 Hz), 8.12 (d, 1H, J=8.24 Hz), 8.36-8.39 (dd, 1H, J1=2.32 Hz, J2=8.24 Hz), 8.87 (d, 1H, J=8.64 Hz), 9.03 (d, 1H, J=1.76 Hz). LC-MS (m/z): M+H=402.1.

Workup

  1. customVolatiles are removed under reduced pressure and crude
  2. additionis diluted
  3. extractionextracted with ethyl acetate
  4. dry with materialOrganic layer is dried over sodium sulphate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (100-200 mesh size)

Sources & evidence

ORD record
ord-fe359b1a43e846ae9e1ecdeb7fde26c3
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

Loading…