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

HRID 354481Notes

Reaction equation

HRID 354481 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[F: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[F: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 69333489ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate

Product 1

HCID 693324003-methoxy-4-[2-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acidYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate (160 mg, 0.28 mmol) in THF (5 mL) was added 0.25 N NaOH (5 mL) and the resulting mixture was the heated under reflux overnight. The mixture was poured into 1 N HCl and the solid was collected. The crude solid was recrystallized from EtOH—CHCl3-n-hexane to give 70 mg (46%) 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acid 258 as a yellow crystalline powder. mp 105-110° C.; IR (KBr) 1687 cm−1; 1H-NMR (DMSO-d6) d 1.00-1.10 (m, 3 H), 2.48 (s, 2H), 3.35-381 (m, 10 H), 4.13-4.14 (m, 2 H), 6.70-9.15 (series of m, 12 H); MS (FAB) m/z 540 (M++1); Anal. Calcd. for C28H30FN3O7.1/2H2O: C, 61.31; H, 5.82; N, 7.47. Found: C, 61.05; H, 5.82; N, 7.47.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. customthe solid was collected
  4. customThe crude solid was recrystallized from EtOH—CHCl3-n-hexane

Sources & evidence

ORD record
ord-2c8d0ff1b13245648eca28cf76b5c22d
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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