Sodium Hydroxide → 3-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid

HRID 1017982Notes

Reaction equation

HRID 1017982 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:35])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[O:24])=[C:18]([O:33][CH3:34])[CH:17]=2)=[CH:9][N:8]=1)C.[OH-].[Na+]>C(O)C>[CH3:34][O:33][C:18]1[CH:17]=[C:16]([CH2:15][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:36])=[O:3])=[N:8][CH:9]=2)=[O:35])[CH:21]=[CH:20][C:19]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 541518273-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid ethyl ester

Product 1

HCID 120505263-(5-{3-Methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acidYield 54.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 3-(5-{3-methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}pyrid-2-yl)-propanoic acid ethyl ester [0.62 g, Reference Example 3(a)] and ethanol (40 ml) was treated with 4% aqueous sodium hydroxide solution (3.2 ml) and then heated to 50° C. After stirring at 50° C. for 7 hours, the reaction mixture was cooled and then left to stand at room temperature over night. The reaction mixture was partially concentrated in vacuo, washed with diethyl ether and then acidified to pH 1.0 by addition of hydrochloric acid (1M). The resultant white solid was collected, washed with water and then dried in vacuo. Recrystallisation from aqueous acetonitrile gave the title compound (0.32 g) as a white crystalline solid, m.p. 191-192° C. (with decomposition). MS: MH+ 463.

Workup

  1. temperaturethe reaction mixture was cooled
  2. waitleft
  3. waitto stand at room temperature over night
  4. concentrationThe reaction mixture was partially concentrated in vacuo
  5. washwashed with diethyl ether
  6. additionacidified to pH 1.0 by addition of hydrochloric acid (1M)
  7. customThe resultant white solid was collected
  8. washwashed with water
  9. customdried in vacuo
  10. customRecrystallisation from aqueous acetonitrile

Sources & evidence

ORD record
ord-7ab7f0a8dbbb477e8c6a93fe44f023fd
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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