Tetrahydrofuran ethanol → HCID 67331566, compound

HRID 1942493Notes

Reaction equation

HRID 1942493 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:19]([O:21]C)=[O:20])[C:16]([CH3:18])=[CH:17][C:12]=2[S:11][CH:10]([CH3:23])[C:9]1=[O:24])=[O:4].O1CCC[CH2:26]1.C(O)C>[OH-].[Na+]>[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:19]([OH:21])=[O:20])[C:16]([CH3:18])=[CH:17][C:12]=2[S:11][C:10]([CH3:23])([CH3:26])[C:9]1=[O:24])=[O:4]

Participants

4

Reactant 2

HCID 21873804Tetrahydrofuran ethanolHCID 58376640HCID 58376640, compound

Product 1

HCID 67331566HCID 67331566, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-{2-[(methoxycarbonyl)amino]ethyl}-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate (210 mg) was dissolved in 1M aqueous sodium hydroxide solution/tetrahydrofuran/ethanol=(2:1:1), and the mixture was stirred at 80° C. for one hour. The reaction solution was concentrated under reduced pressure to remove ethanol. To the concentrated residue was added 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 4-{2-[(methoxycarbonyl)amino]-ethyl}-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid (200 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customto remove ethanol
  3. additionTo the concentrated residue was added 2N hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-05954de3f6064509a0e6acd77829844c
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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