Water → 1-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid

HRID 2421889Notes

Reaction equation

HRID 2421889 reaction equation
[F:1][C:2]([F:27])([F:26])[CH:3]1[CH2:8][CH2:7][N:6]([S:9]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[N:18]=[CH:19][C:20]([C:22]([O:24]C)=[O:23])=[CH:21][C:13]2=3)(=[O:11])=[O:10])[CH2:5][CH2:4]1.O.[OH-].[Li+].O>CO>[F:27][C:2]([F:1])([F:26])[CH:3]1[CH2:8][CH2:7][N:6]([S:9]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[N:18]=[CH:19][C:20]([C:22]([OH:24])=[O:23])=[CH:21][C:13]2=3)(=[O:10])=[O:11])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57896759methyl 1-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

Product 1

HCID 578967981-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (0.280 g, 0.684 mmol) in MeOH (20 mL) was added lithium hydroxide monohydrate (0.144 g, 3.42 mmol) and water (4.00 mL) which provided a white suspension. The reaction was stirred at room temp for 2.5 h. The MeOH was removed under reduced pressure and the resulting aqueous solution was neutralized with concentrated HCl (400 mL) to provide a white solid. The suspension was extracted EtOAc (3×10 mL). The combined organics were dried over anhydrous Na2SO4 and concentrated in vacuo to provide 1-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid as a white solid. The yield was assumed to be 100% for calculation purposes in subsequent reactions. LCMS (+ESI) m/z=396.1 [M+H]+.

Workup

  1. customprovided a white suspension
  2. customThe MeOH was removed under reduced pressure
  3. customto provide a white solid
  4. extractionThe suspension was extracted EtOAc (3×10 mL)
  5. dry with materialThe combined organics were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d8a04b436a747d8a40e3b203cb6794c
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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