Hydrochloric Acid → HCID 15612169, compound

HRID 580419Notes

Reaction equation

HRID 580419 reaction equation
[CH2:1]([C:4]([CH:13]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7]C)=O)[CH:2]=[CH2:3].C[O-].[Na+].Cl>CO>[CH3:12][O:11][C:9]([C:4]1([CH2:1][CH:2]=[CH2:3])[CH:13]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:5]1=[O:7])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 15128663HCID 15128663, compound

Product 1

HCID 15612169HCID 15612169, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of α-(2-propenyl)-[2-(2-aminophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (6.87 g, 17.28 mmol) in 44 ml of methanol with sodium methoxide solution (29.63 ml of a 25 weight percent solution, 129.6 mmol) was refluxed under argon overnight. Although the reaction mixture was nearly homogeneous under reflux, the reaction had not gone to completion (by TLC). After cooling to room temperature, 1M hydrochloric acid was added in several increments (total reaction volume was 200 ml). The crude product was collected by filtration, washed with 90/10 water/methanol, and recrystallized from methanol/water (2 crops) to yield 3.65 g of a white crystalline solid, melting point 175°-176.5° C.

Workup

  1. temperaturewas refluxed under argon overnight
  2. temperatureunder reflux
  3. filtrationThe crude product was collected by filtration
  4. washwashed with 90/10 water/methanol
  5. customrecrystallized from methanol/water (2 crops)

Sources & evidence

ORD record
ord-cad27053bb2043139ed4fb4f03ea4988
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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