Potassium Hydroxide → HCID 25009506, compound

HRID 607121Notes

Reaction equation

HRID 607121 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]=[C:41]([F:43])[C:40]([F:44])=[C:39]([F:45])[CH:38]=2)[O:33][C:32]1=[O:46].[OH-].[K+]>CO>[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:27])([F:28])[F:29])=[CH:22][C:21]=1[CH2:30][N:31]1[C@@H:35]([CH3:36])[C@@H:34]([C:37]2[CH:38]=[C:39]([F:45])[C:40]([F:44])=[C:41]([F:43])[CH:42]=2)[O:33][C:32]1=[O:46]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 25009505HCID 25009505, compound

Product 1

HCID 25009506HCID 25009506, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-2-oxo-5-(3,4,5-trifluorophenyl)-1,3-oxazolidin-3-yl]methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (23 mg, 0.0358 mmol) in MeOH (1 mL) was added 4 M KOH solution (0.5 mL). The reaction was stirred at room temperature for 3 hours, then quenched with 1 N HCl (5 mL) and diluted with EtOAc (15 mL). The aqueous layer was extracted with EtOAc (10 mL), and the combined organic extracts were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by reverse-phase chromatography (C-18, 10 to 95% MeCN/water with 0.1% TFA) to afford 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-2-oxo-5-(3,4,5-trifluorophenyl)-1,3-oxazolidin-3-yl]methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS=629.9 (M+1)+. 1H NMR (CDCl3, 500 MHz, rotamers present) a 8.01-7.93 (m, 2H), 7.70-7.62 (m, 2H), 7.43-7.38 (m, 2H), 7.33-7.30 (m, 1H), 7.14-7.12 (m, 1H), 7.09-7.06 (m, 1H), 6.88-6.80 (m, 2H), 5.39 (d, J=8.0 Hz), 5.15 (d, J=8.0 Hz), 4.92 (d, J=15.6 Hz), 4.86 (d, J=15.6 Hz), 4.16 (d, J=15.8 Hz), 3.95 (d, J=15.8 Hz), 3.86 (m, 3H), 3.72-3.69 (m, 1H), 2.38 (s), 2.34 (s), 0.57 (d, J=6.6 Hz), 0.46 (d, J=6.6 Hz).

Workup

  1. customquenched with 1 N HCl (5 mL)
  2. additiondiluted with EtOAc (15 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (10 mL)
  4. washthe combined organic extracts were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse-phase chromatography (C-18, 10 to 95% MeCN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-0fdb5a9ef7f34874854c3dd1f6d4a753
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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