Hydrochloric Acid → 1-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidine

HRID 895631Notes

Reaction equation

HRID 895631 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([O:25]C)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22380729HCID 22380729, compound

Product 1

HCID 223807041-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidineYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(tert-Butoxycarbonyl)-4-[(2-methoxycarbonylmethoxyphenyl)amino]piperidine (100 mg) was dissolved in methanol (1 ml), added with 1 N aqueous sodium hydroxide (0.55 ml) and stirred at room temperature for 1 hour. The reaction mixture was neutralized with 1 N aqueous hydrochloric acid and extracted twice with ethyl acetate (3 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 72.1 mg of the title compound. Yield: 75%.

Workup

  1. extractionextracted twice with ethyl acetate (3 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0827ad2a133c4dd1bdacd911f2caabe2
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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