Hydrochloric Acid → 3-{4-[2-(4-Methoxy-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoic acid

HRID 1357852Notes

Reaction equation

HRID 1357852 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[O:11][C:7]=2[CH:6]=[C:5]([CH2:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C@H:30]([CH3:37])[CH2:31][C:32]([O:34]CC)=[O:33])=[CH:26][CH:25]=2)=[O:22])[CH:4]=1.[OH-].[Li+].Cl>CO>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[O:11][C:7]=2[CH:6]=[C:5]([CH2:20][C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([CH:30]([CH3:37])[CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:29]=2)=[O:22])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86585957Ethyl (R) 3-{4-[2-(4-methoxy-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoate

Product 1

HCID 181881083-{4-[2-(4-Methoxy-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoic acidYield 74.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (R) 3-{4-[2-(4-methoxy-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoate (0.17 g, Reference Example 8) in methanol was treated with aqueous lithium hydroxide solution (5 mL, 1M) and left to stand for five hours under argon. The mixture was acidified to pH 1 by addition of dilute hydrochloric acid, then partially evaporated, then diluted with more water and then partially evaporated again. The residue was diluted with water to afford a tan solid which was filtered, then dissolved in saturated sodium bicarbonate solution. The solution was washed with ethyl acetate, then acidified to pH1 and then extracted with ethyl acetate several times. The combined ethyl acetate extracts were washed with brine and then evaporated to give the title compound (0.12 g) as a white powder. LC-MS: RT=3.29 minutes (100% by ELSD); MS (ES+), 474 (MH+).

Workup

  1. waitleft
  2. custompartially evaporated
  3. additiondiluted with more water
  4. custompartially evaporated again
  5. additionThe residue was diluted with water
  6. customto afford a tan solid which
  7. filtrationwas filtered
  8. dissolutiondissolved in saturated sodium bicarbonate solution
  9. washThe solution was washed with ethyl acetate
  10. extractionextracted with ethyl acetate several times
  11. washThe combined ethyl acetate extracts were washed with brine
  12. customevaporated

Sources & evidence

ORD record
ord-b7ffe93854694a15ba030848974e1752
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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