Lithium Hydroxide → HCID 22184872, compound

HRID 348073Notes

Reaction equation

HRID 348073 reaction equation
C([O:3][C:4]([CH2:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[NH:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:8])=[O:5])C.[Li+].[OH-].OS([O-])(=O)=O.[Na+]>CO.O>[C:4]([CH2:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[NH:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:8])([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 22184997HCID 22184997, compound

Product 1

HCID 22184872HCID 22184872, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-[ethoxycarbonylmethylcarbonyl][(1,1-dimethylethoxycarbonyl)methyl]aminonaphthalene (730 mg, 1.95 mmol) in methanol (5.0 mL) was added a solution of LiOH (123 mg, 2.91 mmol) in water (3.0 mL). The resulting reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was acidified by 2N NaHSO4 to pH 3, then extracted by ethyl acetate (3×10 mL). The organic layer was evaporated in vacuo to afford 2-[carboxymethylcarbonyl][(1,1-dimethylethoxycarbonyl)methyl]aminonaphthalene (270 mg) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted by ethyl acetate (3×10 mL)
  3. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-b22fc9c369174405909bd12e3eb967e3
Source dataset
uspto-grants-2007_02
Patent number
US07176207B2

Reaction notes

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