Sodium Hydroxide → HCID 14628069, compound

HRID 2165938Notes

Reaction equation

HRID 2165938 reaction equation
Cl.[C:2]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[NH:18])OCC)=[C:7]([CH2:21][CH2:22][CH3:23])[C:6]=1[OH:24])(=[O:4])[CH3:3].N[C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[NH2:37])[C:29]([O:31]CC)=[O:30].[OH-].[Na+]>C(O)C>[C:2]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[NH:18][C:26]3[CH:27]=[C:28]([C:29]([OH:31])=[O:30])[CH:34]=[CH:35][C:36]=3[N:37]=2)=[C:7]([CH2:21][CH2:22][CH3:23])[C:6]=1[OH:24])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 458855Ethyl 3,4-DiaminobenzoateHCID 23042705HCID 23042705, compound

Product 1

HCID 14628069HCID 14628069, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-(4-acetyl-3-hydroxy-2-propylphenoxy)-pentanimidate hydrochloride (3.0 g) and ethyl 3,4-diaminobenzoate (1.4 g) in ethanol (40 ml) was stirred at room temperature for 24 hours. To the mixture was added a solution of sodium hydroxide (1.6 g/30 ml of water) and the resulting mixture was refluxed for 40 minutes. After removal of the solvent under reduced pressure, the mixture was poured into ice-water, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The extract was evaporated and the resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-ethanol (9:1), to give the title compound (2.0 g, 58.1 %) as amorphous powder, mp 98-100 ° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 40 minutes
  2. customAfter removal of the solvent under reduced pressure
  3. additionthe mixture was poured into ice-water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe extract was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography
  9. washeluting with dichloromethane-ethanol (9:1)

Sources & evidence

ORD record
ord-beeac0e7b21f4031aa75b88554ee3a4c
Source dataset
uspto-grants-1990_07
Patent number
US04942245

Reaction notes

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