Lithium Hydroxide → HCID 86615380, compound

HRID 1436567Notes

Reaction equation

HRID 1436567 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]#[CH:15])[N:9]=[C:8]([S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH:7]=1>C1COCC1>[CH3:21][CH:19]([S:16]([C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([NH:12][CH2:13][C:14]#[CH:15])[N:9]=1)[C:5]([OH:22])=[O:4])(=[O:18])=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86615004HCID 86615004, compound

Product 1

HCID 86615380HCID 86615380, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (0.52 mL, 0.52 mmol) to a solution of 2-(propane-2-sulfonyl) -6-prop-2-ynylamino-isonicotinic acid methyl ester (0.102 g, 0.344 mmol) in THF (2 mL) at 0° C. Stir the mixture at room temperature for 3 h and acidify the solution to about pH =2 and concentrate the solvent to one half volume. Partition the residue between ethyl acetate and water, and extract the aqueous layer with ethyl acetate (2×10 mL). Wash the combined organic extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (85%).

Workup

  1. concentrationconcentrate the solvent to one half volume
  2. customPartition the residue between ethyl acetate and water
  3. extractionextract the aqueous layer with ethyl acetate (2×10 mL)
  4. washWash the combined
  5. extractionorganic extract with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-6c07be05228f4cee895252da366a2d10
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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