Nitrogen → HCID 57719158, compound

HRID 1985241Notes

Reaction equation

HRID 1985241 reaction equation
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[CH3:18][C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[CH2:28][CH:27]([CH2:29][CH2:30]OS(C3C=CC(C)=CC=3)(=O)=O)[N:26]([CH2:42][CH2:43][CH3:44])[C:25]2=[O:45])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].N#N.[OH-].[Na+]>C(O)C>[CH3:18][C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[CH2:28][CH:27]([CH2:29][CH2:30][O:17][C:14]3[CH:13]=[CH:12][C:11]([C:6]4([C:4]([OH:3])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10]4)=[CH:16][CH:15]=3)[N:26]([CH2:42][CH2:43][CH3:44])[C:25]2=[O:45])=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57718928HCID 57718928, compoundHCID 57719317HCID 57719317, compound

Product 1

HCID 57719158HCID 57719158, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-hydroxy-phenyl)-cyclopentanecarboxylic acid ethyl ester (0.042 g, 0.179 mmol), toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethyl ester (0.085 g, 0.197 mmol) and 325 mesh K2CO3 (0.050 g, 0.362 mmol) in ethanol (5 mL) was heated at ref lux for under N2 for 16 h. The reaction was then treated with aqueous 5 N NaOH (0.5 mL) and heated to reflux 1.5 h. The reaction mixture was cooled, the solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (10 mL) and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 0.058 g crude acid that was purified by preparative HPLC to afford 0.033 g (40%) 1-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-cyclopentanecarboxylic acid. MS (ES+) Calc'd for C28H37N2O4 (M+1) 465. Found m/z 465 (100%). 1H NMR.

Workup

  1. temperatureheated
  2. temperatureto reflux 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with Et2O
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto afford 0.058 g crude acid that
  9. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-47e13ea165ca4f45ae068b65d00b2349
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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