Hydrochloric Acid → HCID 25010059, compound

HRID 2093233Notes

Reaction equation

HRID 2093233 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][C:10]=2[CH3:19])=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[CH2:30][N:31]1[C@@H:35]([CH3:36])[C@@H:34]([C:37]2[CH:42]=[CH:41][N:40]=[C:39]([CH3:43])[CH:38]=2)[O:33][C:32]1=[O:44].[Li+].[OH-].Cl>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:10]=2[CH3:19])=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][C:21]=1[CH2:30][N:31]1[C@@H:35]([CH3:36])[C@@H:34]([C:37]2[CH:42]=[CH:41][N:40]=[C:39]([CH3:43])[CH:38]=2)[O:33][C:32]1=[O:44]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25010058HCID 25010058, compound

Product 1

HCID 25010059HCID 25010059, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-5-(2-methylpyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (30.1 mg, 0.050 mmol) in 1,4-dioxane (1.5 mL) and water (1.5 mL) was added 1M aqueous LiOH (0.498 mL, 0.498 mmol). The mixture was stirred at room temperature for 4 h. The mixture was acidified with 1N HCl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The crude material was purified by preparative HPLC reverse phase (C-18), eluting with MeCN/water. The fractions were collected and lyophilized to give 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-5-(2-methylpyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]-methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS calc.=591.2; found=591.1 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 8.83 (s, 1 H); 8.02 (s, 1 H); 7.94 (t, J=10.0 Hz, 1 H); 7.72 (s, 0.5 H); 7.69 (t, J=6.0 Hz, 1 H); 7.64 (s, 0.5 H); 7.49-7.43 (m, 3 H); 7.40 (d, J=5.2 Hz, 0.5 H); 7.35 (d, J=5.4 Hz, 0.5 H); 7.31 (m, 1 H); 7.16 (dd, J=2.1, 6.0 Hz, 1H); 7.12 (t, J=8.8 Hz, 1 H); 5.56 (d, J=8.1 Hz, 0.5 H); 5.26 (d, J=8.2 Hz, 0.5H); 4.94 (dd, J=8.7, 15.7 Hz, 1H); 4.77 (br s, 1 H); 4.20 (d, J=15.8 Hz, 0.5 H); 4.00 (d, J=15.7 Hz, 0.5 H); 3.90 (s, 1.5 H); 3.89 (s, 1.5 H); 3.89-3.81 (m, 1 H); 2.82 (s, 1.5 H); 2.81 (s, 1.5 H); 2.41 (s, 1.5 H); 2.36 (s, 1.5 H); 0.62 (d, J=6.5 Hz, 1.5 H); 0.49 (d, J=6.5 Hz, 1.5 H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated in vacuo
  5. customThe crude material was purified by preparative HPLC reverse phase (C-18)
  6. washeluting with MeCN/water
  7. customThe fractions were collected

Sources & evidence

ORD record
ord-61061eb9b20d421ab65df9cad03b7c34
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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