Sodium Hydroxide → HCID 10231423, compound

HRID 1375068Notes

Reaction equation

HRID 1375068 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][C:6]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[CH2:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[O:32])=[C:26]([O:41][CH3:42])[CH:25]=3)=[CH:17][CH:16]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)C.[OH-].[Na+]>C(O)C>[CH3:42][O:41][C:26]1[CH:25]=[C:24]([CH2:23][C:22]([NH:21][C:18]2[CH:17]=[CH:16][C:15]([C:6]3([CH2:5][C:4]([OH:44])=[O:3])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)=[CH:20][CH:19]=2)=[O:43])[CH:29]=[CH:28][C:27]=1[NH:30][C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40])=[O:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69419383HCID 69419383, compound

Product 1

HCID 10231423HCID 10231423, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [2-(4-(2-(3-methoxy-4-(3-o-tolyl-ureido)-phenyl)-acetylamino)-phenyl)-indan-2-yl]-acetic acid ethyl ester (0.06 g, Reference Example 16) in ethanol (10 mL) was treated with aqueous sodium hydroxide (300 μL, 1N) and the mixture was heated at reflux temperature for 8 hours and then left at room temperature overnight and then evaporated. The residue was treated with water (20 mL) and the mixture was warmed to aid dissolution. This solution was acidified to pH 1 by addition of hydrochloric acid (1N) when a precipitate was formed. The mixture was kept at 0° C. for 30 minutes then extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and then evaporated. The residual white solid was subjected to chromatography [gradient HPLC using 50% acetonitrile and water, 1 mL/minute] to give the title compound (0.03 g) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. customevaporated
  4. additionThe residue was treated with water (20 mL)
  5. temperaturethe mixture was warmed
  6. dissolutiondissolution
  7. additionThis solution was acidified to pH 1 by addition of hydrochloric acid (1N) when a precipitate
  8. customwas formed
  9. waitThe mixture was kept at 0° C. for 30 minutes
  10. extractionthen extracted with ethyl acetate
  11. extractionThe ethyl acetate extract
  12. dry with materialwas dried over magnesium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-0e1c713a27134adc9762d662b3540242
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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