Sodium Hydroxide → HCID 10119303, compound

HRID 1375071Notes

Reaction equation

HRID 1375071 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][C:5]1([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:40])[CH2:22][C:23]3[CH:39]=[CH:38][C:26]4[N:27]=[C:28]([NH:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[CH3:37])[O:29][C:25]=4[CH:24]=3)=[CH:16][CH:15]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C(O)C>[C:32]1([CH3:37])[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[NH:30][C:28]1[O:29][C:25]2[CH:24]=[C:23]([CH2:22][C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([C:5]4([CH2:4][C:3]([OH:41])=[O:2])[C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[CH2:7][CH2:6]4)=[CH:15][CH:16]=3)=[O:40])[CH:39]=[CH:38][C:26]=2[N:27]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 69421121HCID 69421121, compound

Product 1

HCID 10119303HCID 10119303, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (1-{4-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-phenyl}-indan-1-yl)-acetic acid methyl ester [0.028 g, Reference Example 9(b)] in ethanol (5 mL) was treated with aqueous sodium hydroxide (0.3 mL, 1N) and the mixture was heated at reflux temperature for 2.5 hours. The mixture was then treated with a further aliquot of aqueous sodium hydroxide (0.15 mL, 1N) and heating at reflux temperature for continued for a further hour. The reaction mixture was concentrated to about 2 mL and then treated with water (12 mL). The resulting solution was acidified to pH 1 by addition of hydrochloric acid (1.75 mL, 1N) with stirring when a solid was deposited. The mixture was ice-cooled and then filtered. The solid was washed three times with water (3 mL) and then dried at 60° C. under vacuum to give the title compound (0.017 g) as a fawn coloured solid. LC-MS: RT=3.69 minutes, MS(ES+): 532(M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 2.5 hours
  3. temperatureheating
  4. temperatureat reflux temperature
  5. waitfor continued for a further hour
  6. concentrationThe reaction mixture was concentrated to about 2 mL
  7. additiontreated with water (12 mL)
  8. additionThe resulting solution was acidified to pH 1 by addition of hydrochloric acid (1.75 mL, 1N)
  9. temperaturecooled
  10. filtrationfiltered
  11. washThe solid was washed three times with water (3 mL)
  12. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-0b9a6e896c574920b35348231b053866
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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