Sodium Hydroxide → HCID 18188090, compound

HRID 1357854Notes

Reaction equation

HRID 1357854 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:38])[CH2:20][C:21]2[CH:37]=[CH:36][C:24]3[N:25]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])[O:27][C:23]=3[CH:22]=2)=[CH:14][CH:13]=1)[CH2:6][C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C.O>[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:38])[CH2:20][C:21]2[CH:37]=[CH:36][C:24]3[N:25]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])[O:27][C:23]=3[CH:22]=2)=[CH:16][CH:17]=1)[CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18188111HCID 18188111, compound

Product 1

HCID 18188090HCID 18188090, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl 6-hydroxy-3-{4-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-phenyl}-hexanoate [460 mg, Reference Example 23 (a)] in a mixture of ethanol (30 mL) and water (10 mL) was treated with sodium hydroxide solution (5mL, 1M) and then heated at 40° C. for 2 hours. The mixture was evaporated and the residue was dissolved in water (50 mL). This solution was washed three times with ethyl acetate, then acidified with dilute hydrochloric acid (a white precipitate was formed) and then extracted three times with ethyl acetate. The combined extracts were washed with brine, then dried and then evaporated. The residual white foam was dissolved in sodium hydroxide solution (50 mL, 0.5M) and the solution was washed twice with ether then acidified with dilute hydrochloric acid. The resulting white precipitate was filtered and then dried to give the title compound (250 mg) as a white solid. LC-MS: RT=2.88 minutes (100% by ELSD); MS (ES+), 488 (MH+).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in water (50 mL)
  3. washThis solution was washed three times with ethyl acetate
  4. customwas formed) and
  5. extractionthen extracted three times with ethyl acetate
  6. washThe combined extracts were washed with brine
  7. customdried
  8. customevaporated
  9. dissolutionThe residual white foam was dissolved in sodium hydroxide solution (50 mL, 0.5M)
  10. washthe solution was washed twice with ether
  11. filtrationThe resulting white precipitate was filtered
  12. customdried

Sources & evidence

ORD record
ord-34a68677637f44c8be33a36ed6f34bff
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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