Hydrochloric Acid → 2-[4-[2-[[[(4-Fluorophenyl)amino]carbonyl]heptylamino]ethyl]phenoxy]-2-methylpropanoic acid

HRID 377734Notes

Reaction equation

HRID 377734 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:35])[N:10]([CH2:18][CH2:19][C:20]2[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28]CC)=[O:27])=[CH:22][CH:21]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:35])[N:10]([CH2:18][CH2:19][C:20]2[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:31])([CH3:32])[C:26]([OH:28])=[O:27])=[CH:22][CH:21]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19356631HCID 19356631, compound

Product 1

HCID 118266282-[4-[2-[[[(4-Fluorophenyl)amino]carbonyl]heptylamino]ethyl]phenoxy]-2-methylpropanoic acidYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.4 g of ethyl 2-(4-[2-(3-[4-fluorophenyl]-1-heptylureido)ethyl]phenoxy)-2-methylpropionate was dissolved in 50 mL of ethanol and 30 mL of 1N aqueous sodium hydroxide was added. The resulting solution was heated at reflux for 30 minutes, cooled to room temperature, acidified with 100 ml of 2N aqueous HCl and extracted with CH2Cl2. The organic extract was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The resulting solid was recrystalized from diethyl ether/hexane to yield 1.1 g of the title compound as a white powder; m.p. 162-4° C.; 1H NMR (CD3OD, δ, 300 MHz): 7.35-6.7 (7H, m, aromatic), 3.48 (2H, t, NCH2), 3.24 (2H, t, NCH2), 2.76 (2H, t, ArCH2), 1.5-1.1 (10H, m, (CH2)5CH3), 1.45 (6H, s, (CH3)2C), 0.83 (3H, t, (CH2)5CH3).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 30 minutes
  3. extractionextracted with CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was recrystalized from diethyl ether/hexane

Sources & evidence

ORD record
ord-615a1f6fe63e4d36b8aecc617430d730
Source dataset
uspto-grants-2000_02
Patent number
US06028109

Reaction notes

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