Sodium Hydroxide → HCID 9934999, compound

HRID 1883706Notes

Reaction equation

HRID 1883706 reaction equation
[C:1]1([CH3:38])[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]=[CH:23][C:24]([CH:30]([CH3:37])[CH2:31][C:32]([O:34]CC)=[O:33])=[C:25]4[C:29]=3[CH2:28][CH2:27][CH2:26]4)=[O:19])[CH:14]=[CH:13][C:11]=2[N:12]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH3:38])[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]=[CH:23][C:24]([CH:30]([CH3:37])[CH2:31][C:32]([OH:34])=[O:33])=[C:25]4[C:29]=3[CH2:28][CH2:27][CH2:26]4)=[O:19])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23508314HCID 23508314, compound

Product 1

HCID 9934999HCID 9934999, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-{7-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-indan-4-yl}-butanoat [0.754 g, Reference Example 1(a)] in ethanol (150 mL) was treated with aqueous sodium hydroxide solution (4 mL, 1M). The reaction mixture was allowed to stand at room temperature for 48 hours, then heated at reflux temperature for 1 hour and then evaporated. The residue was dissolved in a mixture of acetonitrile and water (35:65, v/v) and the resulting solution was acidified to pH 2 by addition of trifluoroacetic acid. The resulting solid was filtered and subjected to reversed phase HPLC (Hypersil Elite C18 column, 10×2 cm, using acetonitrile and water mixtures containing 0.1% trifluoroacetic acid and running a linear gradient of +1% acetonitrile/minute, starting with 35% acetonitrile) to give the title compound (396 mg) as a white solid. LC-MS: RT=3.37 minutes (>98% by ELSD); MS(ES+), 484(MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 hour
  3. customevaporated
  4. dissolutionThe residue was dissolved in a mixture of acetonitrile and water (35:65
  5. additionv/v) and the resulting solution was acidified to pH 2 by addition of trifluoroacetic acid
  6. filtrationThe resulting solid was filtered
  7. additioncontaining 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-5c3e94f18be943f1be73f727425ba9fd
Source dataset
uspto-grants-2004_07
Patent number
US06762199B2

Reaction notes

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