Lithium Hydroxide → HCID 68814764, compound

HRID 732434Notes

Reaction equation

HRID 732434 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[CH:12]=[C:11]([NH:13][CH:14]2[CH2:17][CH2:16][CH2:15]2)[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]=1)=[O:6]>C1COCC1>[CH3:22][CH2:21][O:20][C:18]([C:9]1[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:12]=[C:11]([NH:13][CH:14]2[CH2:15][CH2:16][CH2:17]2)[N:10]=1)=[O:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68814738HCID 68814738, compound

Product 1

HCID 68814764HCID 68814764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (0.80 mL, 0.802 mmol) to a solution of 6-cyclobutylaminopyridine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester (0.223 g, 0.802 mmol) in THF (2 mL) at 0° C. Stir for 1 h, acidify the solution to about pH=2, concentrate the solvent to one half volume. Partition the residue between ethyl acetate and water, and extract the aqueous layer with ethyl acetate (2×15 mL). Wash the combined organic extracts with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound.

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 (2×15 mL)
  4. washWash the combined organic extracts with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-aff36c847edb4b1cab4dad9150b5ca60
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…