Sodium Hydroxide → (2-{4-[2-(2-o-Tolylamino-benzoxazol-6-yl)-acetylamino]-phenyl}-indan-2-yl)-acetic Acid

HRID 1375067Notes

Reaction equation

HRID 1375067 reaction equation
C([O:3][C:4](=[O:42])[CH2:5][C:6]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:41])[CH2:23][C:24]3[CH:40]=[CH:39][C:27]4[N:28]=[C:29]([NH:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[CH3:38])[O:30][C:26]=4[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>[C:33]1([CH3:38])[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH:31][C:29]1[O:30][C:26]2[CH:25]=[C:24]([CH2:23][C:22]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([C:6]4([CH2:5][C:4]([OH:42])=[O:3])[CH2:14][C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[CH2:7]4)=[CH:16][CH:17]=3)=[O:41])[CH:40]=[CH:39][C:27]=2[N:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69417626(2-(4-(2-(2-o-Tolylamino-benzoxazol-6-yl)-acetylamino)-phenyl)-indan-2-yl)-acetic acid ethyl ester

Product 1

HCID 10119302(2-{4-[2-(2-o-Tolylamino-benzoxazol-6-yl)-acetylamino]-phenyl}-indan-2-yl)-acetic AcidYield 24.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2-(4-(2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino)-phenyl)-indan-2-yl)-acetic acid ethyl ester [0.297 g, Reference Example 9(a)] in ethanol (10 mL) was treated with aqueous sodium hydroxide (1.61 mL, 1N) and the mixture was heated at reflux temperature for 6 hours and then left at room temperature overnight and then evaporated. The residue was treated with water (30 mL) and the resulting mixture was acidified to pH 1 by addition of hydrochloric acid (1N) then extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and then evaporated. The residue was dissolved in hot acetonitrile and the solution was treated with charcoal then filtered. The filtrate was evaporated to give the title compound (0.07 g) as a biscuit coloured solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 6 hours
  3. customevaporated
  4. additionThe residue was treated with water (30 mL)
  5. additionthe resulting mixture was acidified to pH 1 by addition of hydrochloric acid (1N)
  6. extractionthen extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. dry with materialwas dried over magnesium sulfate
  9. customevaporated
  10. dissolutionThe residue was dissolved in hot acetonitrile
  11. additionthe solution was treated with charcoal
  12. filtrationthen filtered
  13. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5ac7d2603fc84815b8651887ff96f746
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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