Sodium Bicarbonate → HCID 70431314, compound

HRID 652964Notes

Reaction equation

HRID 652964 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][O:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:19])[CH:6]=[CH:7][C:8]=1[O:9]COCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[CH:25]([O:24][CH2:23][CH2:22][CH2:21][NH:20][C:18](=[O:19])[CH:17]=[CH:16][C:5]1[CH:6]=[CH:7][C:8]([OH:9])=[C:3]([O:2][CH3:1])[CH:4]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 57252035HCID 57252035, compound

Product 1

HCID 70431314HCID 70431314, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 378 mg (0.75 mmol) of the amide compound in methanol (10 ml) was added 19 mg (0.1 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was heated and refluxed for 1 hour. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, which .was extracted with ethyl acetate, and the organic layer was concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with chloroform - methanol (50 : 1), to give 230 mg (0.55 mmol) of 3-[3-[3-methoxy-4-hydroxyphenyl)-2-propenoyl]aminopropyl benzhydryl ether. Spectrophotometric data of the product support the structure shown below. ##STR86##

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 1 hour
  3. extraction.was extracted with ethyl acetate
  4. concentrationthe organic layer was concentrated by evaporation under reduced pressure
  5. washeluted with chloroform - methanol (50 : 1)

Sources & evidence

ORD record
ord-52f2834cad254a41a0c4676fc0272311
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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