Hydrochloric Acid → 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acid

HRID 350538Notes

Reaction equation

HRID 350538 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:20](=[O:41])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=1)[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:20](=[O:41])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69332900ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate

Product 1

HCID 693333643-methoxy-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate (550 mg, 0.98 mmol) in THF (15 mL) was added 0.25 N NaOH (15 mL). The resulting mixture was then heated under reflux for 2 days. The mixture was poured into 1 N HCl and the solid was collected. The crude solid was recrystallized from EtOH—CHCl3 to give 182 mg (35%) 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acid 256 as a white crystalline powder. mp 115–118° C.; IR (KBr) 1707 cm−; 1H-NMR (DMSO-d6) δ 1.02–1.12 (m, 3 H), 2.25 (s, 3 H), 2.50 (s, 2 H), 3.35–3.89 (m, 10 H), 4.11–4.16 (m, 2H), 6.71–8.56 (series of m, total 12H), 12.65 (br s, 1H); MS (FAB) m/z 536 (M30 +1); Anal. Calcd for C29H33N3O7.3/4H2O: C, 63.43; H, 6.33; N, 7.65. Found: 63.34; H, 6.28; N, 7.28.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 2 days
  3. customthe solid was collected
  4. customThe crude solid was recrystallized from EtOH—CHCl3

Sources & evidence

ORD record
ord-c9de37af997e4b7b8939f1d7b4434f57
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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