Hydrochloric Acid → HCID 25010576, compound

HRID 2093169Notes

Reaction equation

HRID 2093169 reaction equation
[F:1][C:2]([F:50])([F:49])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:31]=[C:32]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([O:46]C)=[O:45])=[CH:40][CH:39]=4)[CH:33]=[CH:34][C:35]=3[O:36][CH3:37])[C@H:14]2[CH3:48])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:31]=[C:32]([C:38]4[CH:39]=[CH:40][C:41]([C:44]([OH:46])=[O:45])=[CH:42][CH:43]=4)[CH:33]=[CH:34][C:35]=3[O:36][CH3:37])[C@H:14]2[CH3:48])[CH:4]=[C:3]([C:2]([F:1])([F:50])[F:49])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 86630538HCID 86630538, compound

Product 1

HCID 25010576HCID 25010576, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2″-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4′-methoxy-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (10 mg, 0.014 mmol), aqueous potassium hydroxide (150 μL, 3M, 0.45 mmol) and ethanol (1 mL) were stirred at 20° C. for 2 hours and 30 minutes to complete the hydrolysis. The reaction mixture was acidified by HCl (aq., 1N) and then basified by sodium bicarbonate. Volatiles were removed under reduced pressure. The resulting mixture was worked up with ethyl acetate, washed with brine. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to an oil. This oil was purified by preparative TLC on SiO2 (eluted with 50% EtOAc in hexanes) to afford 2″-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4′-methoxy-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS calc.=697.15; found=698.03 (M+1)+. 1H NMR signals are doubled because of atropisomerism 1H NMR (CDCl3, 500 MHz) δ 8.16-8.11 (m, 2H), 7.83 (d, J=8.0 Hz, 1H), 7.74-7.69 (m, 2H), 7.69-7.65 (m, 2.5H), 7.65-7.61 (m, 1.5H), 7.57 (s, 1H), 7.48-7.42 (m, 2.0H), 7.11 (dd, J=8.8, 2.5 Hz, 1H), 5.57 (d, J=8.0 Hz, 0.5H), 5.17 (d, J=8.0 Hz, 0.5H), 4.97 (d, J=15.5 Hz, 0.5H), 4.93 (d, J=15.5 Hz, 0.5H), 4.16 (d, J=16 Hz, 0.5H), 3.95 (d, J=16.0 Hz, 0.5H), 3.88, 3.87 (s, 3H), 3.80-3.72 (m, 1H), 0.55 (d, J=6.5 Hz, 1.5H), 0.41 (d, J=6.5 Hz, 1.5H).

Workup

  1. customthe hydrolysis
  2. customVolatiles were removed under reduced pressure
  3. washwashed with brine
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThis oil was purified by preparative TLC on SiO2 (eluted with 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f75e264b2a634e7c96b6a879c8c93ca4
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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