Hydrochloric Acid → HCID 86745991, compound

HRID 654344Notes

Reaction equation

HRID 654344 reaction equation
[CH2:1]([NH:16][C:17](=[O:36])[CH:18]=[CH:19][CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28]C(OCC)=O)=[C:24]([O:34][CH3:35])[CH:23]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])\[CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([NH:16][C:17](=[O:36])[CH:18]=[CH:19][CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([O:34][CH3:35])[CH:23]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])\[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86745992HCID 86745992, compound

Product 1

HCID 86745991HCID 86745991, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.06 g of 5-(4'-ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid (E,E)-farnesylamide in 40 ml of methanol is added 20 ml of 2N aqueous solution of sodium hydroxide. The mixture is stirred at room temperature for one hour. The reaction mixture, after acidified with 1N hydrochloric acid, is extracted with chloroform. The organic layer is washed with water and dried over sodium sulfate. The solvent is distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with chloroform is obtained 1.67 g of 5-(4'-hydroxy3'-methoxyphenyl)pentadienoic acid (E,E)-farnesylamide (13). Spectroscopic data of the product support the structure of the formula (13) below.

Workup

  1. extractionis extracted with chloroform
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent is distilled off under reduced pressure
  5. washFrom the fraction eluted with chloroform

Sources & evidence

ORD record
ord-c4152083cfaf4a6c9169776058b7cfae
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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