Sodium Hydroxide → HCID 13560551, compound

HRID 638068Notes

Reaction equation

HRID 638068 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH2:6][NH:7][C:8]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:9])C.[OH-].[Na+]>C(O)C>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([CH:5]([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)=[O:9])[C:4]([OH:31])=[O:3])[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135605252-(3,4-Dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid ethyl ester

Product 1

HCID 13560551HCID 13560551, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18.4 g of 2-(3,4-dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid ethyl ester, 50 ml of ethanol, and 65 ml of 10% sodium hydroxide was refluxed for 2 hours, concentrated to remove ethanol, and diluted with water. The aqueous layer was washed with ethyl acetate, acidified with excess 6N hydrochloric acid, and the product was extracted with ethyl acetate, dried, and evaporated. Trituration of the residue with ether provided 10.9 g of insoluble 2-(3,4-dimethoxyphenyl)3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid, mp 151°-153°. Crystallization from ethyl acetate gave the analytical sample, mp 150°-152°.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationconcentrated
  3. customto remove ethanol
  4. additiondiluted with water
  5. washThe aqueous layer was washed with ethyl acetate
  6. extractionthe product was extracted with ethyl acetate
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-be245b01d7f4482d89b1af8f46b0a375
Source dataset
uspto-grants-1985_12
Patent number
US04559403

Reaction notes

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