Trifluoroacetic acid → HCID 86695435, compound

HRID 525545Notes

Reaction equation

HRID 525545 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C@H:17]3[O:21]C(C)(C)[N:19]([C:24](=[O:28])[CH:25]([F:27])[F:26])[C@@H:18]3[CH2:29][F:30])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].FC(F)(F)C(O)=O>C(Cl)Cl.C(=O)(O)[O-]>[CH3:3][N:2]([CH2:4][C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C@@H:17]([OH:21])[C@@H:18]([NH:19][C:24](=[O:28])[CH:25]([F:26])[F:27])[CH2:29][F:30])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695433HCID 86695433, compound

Product 1

HCID 86695435HCID 86695435, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{(4S,5R)-5-[4-(6-Dimethylaminomethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone (0.070 g, 0.166 mmol) in CH2Cl2 (5 mL) is added trifluoroacetic acid (1.0 mL). The resulting reaction mixture is stirred at room temperature for 5 hours. Concentrated to get the crude residue and diluted with aqueous bicarbonate solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by combi-flash chromatography using 15% methanol in CH2Cl2 as an eluent. Obtained solid is washed with n-pentane and diethyl ether to afford the title compound (0.030 g). 1HNMR (400 MHz, DMSO-d6) δ: 2.44 (s, 6H), 3.90 (bs, 2H), 4.28-4.30 (m, 1H), 4.31-4.33 (m, 0.5H), 4.41-4.45 (m, 0.5H), 4.54-4.55 (m, 0.5H), 4.65-4.68 (m, 0.5H), 4.89 (t, J=4.0 Hz, 1H), 5.93 (d, J=4.56 Hz, 1H), 6.20 (t, J=53.76 Hz, 1H), 7.47 (d, J=8.24 Hz, 2H), 7.53 (d, J=8.16 Hz, 1H), 7.72 (d, J=8.24 Hz, 2H), 8.11-8.13 (m, 1H), 8.84-8.87 (m, 2H). LC-MS (m/z): [M+H]=382.1.

Workup

  1. customThe resulting reaction mixture
  2. concentrationConcentrated
  3. customto get the crude residue
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer is dried over sodium sulphate, solvent
  6. customis evaporated in vacuo
  7. custompurified by combi-flash chromatography
  8. customObtained solid
  9. washis washed with n-pentane and diethyl ether

Sources & evidence

ORD record
ord-93e144535c1544af9ddfa5dad8e3fcbb
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

Loading…