Reaction #1973962

ord-70d5024c6fa54b849460b2a52395ed07

Reaction equation

COC(=O)c1cc([N+](=O)[O-])cc(C(C)(C)C)c1O
product
COC(=O)c1cc([N+](=O)[O-])cc(C(C)(C)C)c1O
methyl 3-tert-butyl-2-hydroxy-5-nitrobenzoate
Cc1ccccc1
toluene
C=CC(=O)O
acrylic acid
C=CC(=O)O
acrylic acid
COC(=O)c1cc(NCCC(=O)O)cc(C(C)(C)C)c1OC
crude title compound
COC(=O)c1cc(NCCC(=O)O)cc(C(C)(C)C)c1OC
3-(3-tert-butyl-4-methoxy-5-(methoxycarbonyl)phenylamino) propanoic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThis mixture was heated
  2. 2
    Temperatureto reflux
  3. 3
    workup.ADDITIONadded every 3 h
  4. 4
    TemperatureThe mixture was then refluxed for 24 h
  5. 5
    TemperatureThe mixture was then cooled
  6. 6
    Concentrationconcentrated under vacuum to dryness

Procedure

The product from Example 5, Part C (16.44 g, 69.3 mmol) was dissolved in toluene (200 mL). This mixture was heated to reflux and acrylic acid added over time (1 mL of acrylic acid added every 3 h, 5.23 mL total, 76.2 mmol). The mixture was then refluxed for 24 h. The mixture was then cooled and concentrated under vacuum to dryness to yield an oil as the crude title compound that was used directly in the next reaction.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08501238B2uspto-grants-2013_08