3,3-Dimethylbutanoyl chloride → Methyl [3-(2,2-dimethylpropionamido)-4-hydroxyphenyl]acetate

HRID 48149

Reaction equation

HRID 48149 reaction equation
[C:1](=[O:4])([O-])O.[Na+].[CH3:6][O:7][C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH2:17])[CH:11]=1.[C:19](CC(Cl)=O)([CH3:22])([CH3:21])[CH3:20]>COCCOC>[CH3:20][C:19]([CH3:22])([CH3:21])[C:1]([NH:17][C:12]1[CH:11]=[C:10]([CH2:9][C:8]([O:7][CH3:6])=[O:18])[CH:15]=[CH:14][C:13]=1[OH:16])=[O:4]

Participants

5

Reactant 3

HCID 815143,3-Dimethylbutanoyl chlorideHCID 516892Sodium BicarbonateHCID 1475136Methyl 2-(3-amino-4-hydroxyphenyl)acetate

Product 1

HCID 22742103Methyl [3-(2,2-dimethylpropionamido)-4-hydroxyphenyl]acetate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium hydrogen carbonate (19 g, 0.23 mol) was suspended in 1,2-dimethoxyethane (180 ml), and methyl(3-amino-4-hydroxyphenyl)acetate [from step 4] (26.3 g, 0.145 mole) was added. To this mixture was added, dropwise, a solution of tert-butylacetyl chloride in 1,2-dimethoxyethane (45 ml), over 2 hours. Once the addition was complete, the mixture was stirred at room temperature for 1 hour. The mixture was filtered, the inorganic solid washed with ethyl acetate (3×50 ml) and the filtrate and washings were combined and concentrated. Trituration of the product with hexane gave methyl [3-(2,2-dimethylpropionamido)-4-hydroxyphenyl]acetate (40.1 g) as an off-white solid, m.p. 112-113° C.

Workup

  1. additionTo this mixture was added
  2. additionOnce the addition
  3. filtrationThe mixture was filtered
  4. washthe inorganic solid washed with ethyl acetate (3×50 ml)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-243b0118cca64c148b39063df98fba65
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Linked notes

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