Lithium Hydroxide → 2-sec-Butylamino-6-(1,1-dioxo-1lambda6[1,2]thiazinan-2-yl)-isonicotinic acid

HRID 1436574Notes

Reaction equation

HRID 1436574 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][S:13]2(=[O:19])=[O:18])[N:9]=[C:8]([NH:20][CH:21]([CH2:23][CH3:24])[CH3:22])[CH:7]=1>C1COCC1>[CH:21]([NH:20][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][S:13]2(=[O:19])=[O:18])[N:9]=1)[C:5]([OH:25])=[O:4])([CH2:23][CH3:24])[CH3:22]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 688144262-sec-Butylamino-6-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-isonicotinic acid methyl ester

Product 1

HCID 688143152-sec-Butylamino-6-(1,1-dioxo-1lambda6[1,2]thiazinan-2-yl)-isonicotinic acidYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (4.0 mL, 3.88 mmol) to a solution of 2-sec-butylamino-6-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-isonicotinic acid methyl ester (0.590 g, 1.80 mmol) in THF (5 mL) at 0° C. Stir for 2 h at room temperature and acidify the mixture to about pH =2 and concentrate. Extract the residue with ethyl acetate (3×40 mL) and wash the combined extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (0.377 g, 74%).

Workup

  1. concentrationconcentrate
  2. extractionExtract the residue with ethyl acetate (3×40 mL)
  3. washwash the
  4. extractioncombined extract with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-6ba7bb0245c14022a34694a75f84e31e
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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