Triethylamine → HCID 23512019, compound

HRID 354474Notes

Reaction equation

HRID 354474 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][NH2:17])[C:6]([O:8]CC)=[O:7].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:37][C:38](O)=[O:39])[CH:23]=[CH:24][C:25]=1[NH:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36])=[O:28].CCN(CC)CC.[OH-].[Na+]>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][C:38](=[O:39])[CH2:37][C:22]1[CH:23]=[CH:24][C:25]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])=[O:28])=[C:20]([O:19][CH3:18])[CH:21]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 10922629HCID 10922629, compoundHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acid

Product 1

HCID 23512019HCID 23512019, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-methoxy-4-(2-aminoethoxy)benzoate (250 mg, 1.04 mmol) and pentafluorophenyl ester of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (500 mg, 1.04 mmol) was added Et3N (210 μl, 3.01 mmol), and the resulting mixture was stirred for 2 days. 0.25 N NaOH (20 ml) and THF (20 mL) was added to the mixture and the resulting mixture was heated under reflux overnight. After cooling, the mixture was evaporated and the residue was acidified by the addition of 1 N HCl. The mixture was extracted with CHCl3, and the extract was washed with brine, dried over Na2SO4, and evaporated. The obtained crude solid was recrystallized from CHCl3 to give 110 mg (20% for 2 steps) 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]aminoethoxy]benzoic acid 255 as a white crystalline powder. mp 180-181° C.; IR (KBr) 1687 cm−1; 1H-NMR (DMSO-d6) d 2.24 (s, 3 H), 3.37 (s, 2 H), 3.38 (s, 2 H), 3.41-3.50 (m, 2 H), 3.81 (s, 3 H), 3.83 (s, 3 H), 4.06-4.08 (m, 2 H), 6.76-8.55 (series of m, total 12 H); MS (FAB) m/z 508 (M++1); Anal. Calcd. for C27H29N3O7.1/2H2O: C, 62.78; H, 5.85; N, 8.13. Found: C, 62.46; H, 5.69; N, 8.03.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customthe mixture was evaporated
  5. additionthe residue was acidified by the addition of 1 N HCl
  6. extractionThe mixture was extracted with CHCl3
  7. washthe extract was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe obtained crude solid
  11. customwas recrystallized from CHCl3

Sources & evidence

ORD record
ord-acdca2c46da94c188f66cbb4e0c37cc1
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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