Methanol → HCID 13560552, compound

HRID 638069Notes

Reaction equation

HRID 638069 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH2:15][NH:16][C:17]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)=[O:18])[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(=O)(=O)(O)O.[CH3:35]O>>[CH3:35][O:13][C:12](=[O:14])[CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:15][NH:16][C:17]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13560551HCID 13560551, compound

Product 1

HCID 13560552HCID 13560552, compound

Procedure

A solution of 23.3 g of 2-(3,4-dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid and 15.5 ml of concentrated sulfuric acid in 300 ml of methanol was refluxed for 6 hours and evaporated to dryness. The residue was partitioned between ethyl acetate and dilute sodium bicarbonate solution and the organic layer was dried and evaporated to give 15.5 g of crude 2-(3,4-dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid methyl ester. Crystallization from ethyl acetate provided the analytical sample, mp 92°-93°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and dilute sodium bicarbonate solution
  3. customthe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-fbff6ec90f154543b0b5f0a3dbac063f
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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