Sodium Hydroxide → HCID 23508312, compound

HRID 1883708Notes

Reaction equation

HRID 1883708 reaction equation
[C:1]1([CH3:36])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][C:18]([NH:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[CH:26]([CH2:30][C:31]([O:33]CC)=[O:32])[CH2:25][CH2:24]4)=[O:19])[CH:14]=[CH:13][C:11]=2[N:12]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH3:36])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][C:18]([NH:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[CH:26]([CH2:30][C:31]([OH:33])=[O:32])[CH2:25][CH2:24]4)=[O:19])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86590039HCID 86590039, compound

Product 1

HCID 23508312HCID 23508312, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl {5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-indan-1-yl}-acetate [0.255 g, Reference Example 1(b)] in ethanol, under a nitrogen atmosphere, was treated with sodium hydroxide solution (1.6 mL, 1M) and the mixture was heated at reflux temperature for 1.5 hour. The reaction mixture was evaporated and the residual orange oil was treated with water (20 ml) and a few drops of tetrahydrofuran. The mixture was filtered and the filtrate was acidified to pH 1 by addition of concentrated hydrochloric acid. The resulting precipitate was filtered at 0° C., then washed twice with a little water and then dried in a dessicator at 50° C. to give the title compound (0.239 g) as a cream coloured solid. LC-MS: RT=3.22 minutes (100% by ELSD); MS(ES+) 456(MH+), 478(MNa+)

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1.5 hour
  3. customThe reaction mixture was evaporated
  4. additionthe residual orange oil was treated with water (20 ml) and a few drops of tetrahydrofuran
  5. filtrationThe mixture was filtered
  6. additionthe filtrate was acidified to pH 1 by addition of concentrated hydrochloric acid
  7. filtrationThe resulting precipitate was filtered at 0° C.
  8. washwashed twice with a little water
  9. customdried in a dessicator at 50° C.

Sources & evidence

ORD record
ord-ba30fd4c6aa747bd82ba48a34a0eee44
Source dataset
uspto-grants-2004_07
Patent number
US06762199B2

Reaction notes

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