Sodium Hydroxide → HCID 58674369, compound

HRID 1994145Notes

Reaction equation

HRID 1994145 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[C:18]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[C:18]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58674451HCID 58674451, compound

Product 1

HCID 58674369HCID 58674369, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[3-({2-[(tert-butoxycarbonyl)amino]pyridin-4-yl}oxy)phenyl]propanoate (427 mg, 1.15 mmol) in MeOH (10 mL) and THF (5 mL), was added 1M NaOH solution (4.59 mL, 4.49 mmol). The reaction was stirred for 18 h. The solvents were evaporated and the residue was dissolved in water. The solution was acidified to pH=3 by addition of 1N HCl. The precipitate was filtered off and washed with water and then hexane, then dried under vacuum to yield the title compound as a white solid (333 mg, 81%). LCMS: (FA) ES+ 359.1 (M+1), ES− 357.0 (M−1).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in water
  3. additionThe solution was acidified to pH=3 by addition of 1N HCl
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. dry with materialhexane, then dried under vacuum

Sources & evidence

ORD record
ord-d31b187055e24270ba3c4a69f1ba3b46
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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