Citric Acid → HCID 22710247, compound

HRID 352725Notes

Reaction equation

HRID 352725 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=2)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CCC.CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=2)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22709700HCID 22709700, compound

Product 1

HCID 22710247HCID 22710247, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

At room temperature, methyl 4-[2-(tert-butoxycarbonylamino)pyridin-5-yl]benzoate (250 mg) was suspended in a mixed solvent of tetrahydrofuran (10 ml) and methanol (10 ml), followed by the addition of a 1N aqueous sodium hydroxide solution (8 ml). The resulting mixture was stirred for 5 hours. The reaction mixture was made weakly acidic with an aqueous citric acid solution, followed by the addition of saturated saline and n-butanol to separate the organic layer. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off, whereby the title compound (120 mg, 49%) was obtained as a crude purified product.

Workup

  1. customAt room temperature
  2. customto separate the organic layer
  3. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-735e703b76214f43854957c20b06e8e5
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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