Sodium Hydroxide → HCID 70024301, compound

HRID 412475Notes

Reaction equation

HRID 412475 reaction equation
C[O:2][C:3]([CH2:5][CH:6]([NH:34][C:35]([CH2:37][CH2:38][CH2:39][C:40]([O:42]C)=[O:41])=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:33])[CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:23][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[N:21][C:20]=3[CH:32]=2)=[CH:9][CH:8]=1)=[O:4].[OH-].[Na+]>O1CCCC1>[C:3]([CH2:5][CH:6]([NH:34][C:35]([CH2:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:33])[CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:23][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[N:21][C:20]=3[CH:32]=2)=[CH:9][CH:8]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 54022644HCID 54022644, compound

Product 1

HCID 70024301HCID 70024301, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(2-methoxycarbonyl-1-{4-[2-(2-o-tolylamino-benzoxazol-5-yl)-acetylamino]-phenyl}-ethylcarbamoyl)-butyrate (0.31 g, Reference Example 12) aqueous sodium hydroxide solution (2.64 ml, 1M) and tetrahydrofuran was heated at reflux temperature for 3 hours. The mixture was then treated with a further aliquot of aqueous sodium hydroxide solution (2.64 ml, 1M) and heating at reflux temperature was continued for a further 3 hours. The reaction mixture was evaporated and the residue was dissolved in water. The pH of this solution was adjusted to 1-2 by addition of concentrated 1,57 hydrochloric acid. The resulting solid was filtered, then washed well with water, then dried and then recrystallised from aqueous iso-butanol. The crystalline solid was washed with pentane and then dried at 100° C. under vacuum to give the title compound (0.13 g) as colourless crystals, m.p. 255.6-257.1° C. [Elemental analysis: Found: C, 64.51; H, 5.41; N, 10.03; H2O, 1.58%. Calculated for C30H30N4O7.0.5H2O: C, 63.43; H, 5.51; N, 9.87; H2O, 1.59%].

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. temperatureheating
  4. temperatureat reflux temperature
  5. customThe reaction mixture was evaporated
  6. dissolutionthe residue was dissolved in water
  7. additionThe pH of this solution was adjusted to 1-2 by addition
  8. concentrationof concentrated 1,57 hydrochloric acid
  9. filtrationThe resulting solid was filtered
  10. washwashed well with water
  11. customdried
  12. customrecrystallised from aqueous iso-butanol
  13. washThe crystalline solid was washed with pentane
  14. customdried at 100° C. under vacuum

Sources & evidence

ORD record
ord-688c5cca473e401bafb013dc9da55cf4
Source dataset
uspto-grants-2003_05
Patent number
US06562851B2

Reaction notes

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