Sodium Hydroxide → HCID 54108350, compound

HRID 1196279Notes

Reaction equation

HRID 1196279 reaction equation
[C:1]([O:5][C:6]([N:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([O:19]C)=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([OH:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54064627Methyl 2-[[(1,1-dimethylethoxy)carbonyl]methylamino]benzeneacetate

Product 1

HCID 54108350HCID 54108350, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl [2-(N-tert-butoxycarbonyl-N-methylamino)phenyl]acetate (3.5 g) in ethanol (50 cc) is treated with normal sodium hydroxide solution (15 cc) at 80° C. for 4 hours. The reaction mixture is concentrated under reduced pressure (2.7 kPa). The residue is taken up with water (100 cc) and the solution, acidified to pH 1 with 4N hydrochloric acid, is extracted with ethyl acetate (2×100 cc). The combined organic phases are dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give [2-(N-tert-butoxycarbonyl-N-methylamino)phenyl]acetic acid (2.85 g) in the form of a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure (2.7 kPa)
  2. extractionis extracted with ethyl acetate (2×100 cc)
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-15ff6ee8e7d1472ead7c4cf1ff483f0c
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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