Methanol → 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid

HRID 2421883Notes

Reaction equation

HRID 2421883 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20]([O:22]C)=[O:21])=[CH:19][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.O.[OH-].[Li+]>C1COCC1>[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20]([OH:22])=[O:21])=[CH:19][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67243254methyl 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

Product 1

HCID 578967851-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (270 mg, 0.808 mmol) in THF (10 mL)/MeOH (10 mL)/water (10 mL) was added lithium hydroxide (38.7 mg, 1.615 mmol). The reaction was stirred at room temperature for 16 hours. LCMS analysis of the reaction mixture identified the molecular ion corresponding to product. The reaction mixture was concentrated in vacuo to remove the organic solvents. The aqueous layer was acidified with 1N aqueous HCl (10 mL), which resulted in a white precipitate formation. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organics were dried over anhydrous Na2SO4 and concentrated in vacuo to provide 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid (230 mg, 0.718 mmol, 89% yield) as an off-white solid that was used without further purification. LCMS (+ESI) m/z=321.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the organic solvents
  3. customresulted in a white precipitate formation
  4. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
  5. dry with materialThe combined organics were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31ad98cd7a2547b1baedf33882d23696
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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