Hydrochloric Acid → HCID 18404702, compound

HRID 1018012Notes

Reaction equation

HRID 1018012 reaction equation
C([O:3][C:4](=[O:42])[CH2:5][CH:6]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:41])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=2)=[CH:15][CH:14]=1)[CH2:7][C:8]([O:10]CC)=[O:9])C.[OH-].[Na+].Cl>CO>[CH3:40][O:39][C:24]1[CH:23]=[C:22]([CH2:21][C:20]([NH:19][C:16]2[CH:15]=[CH:14][C:13]([CH:6]([CH2:5][C:4]([OH:42])=[O:3])[CH2:7][C:8]([OH:10])=[O:9])=[CH:18][CH:17]=2)=[O:41])[CH:27]=[CH:26][C:25]=1[NH:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53952853HCID 53952853, compound

Product 1

HCID 18404702HCID 18404702, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}phenyl)-pentanedioic acid di-ethyl ester [8.40 g, Reference Example 12(x)] and methanol (400 ml) was heated to 40° C. and then treated with 10% aqueous sodium hydroxide solution (110 ml). After stirring at 40° C. for 1 hour, the reaction mixture was cooled 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 ethanol gave the title compound as a white crystalline solid (4.7 g), m.p. 218-220° C. [Elemental analysis:—C, 64.5; H, 5.6; N, 7.9%. Calculated for C28H29N3O7:—C, 64.7; H, 5.6; N, 8.1%].

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe resultant white solid was collected
  3. washwashed with water
  4. customdried in vacuo
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-104f1db3f5d04146a6288663ee5b26f5
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

Loading…