2,4-Dimethoxyphenyl isocyanate → 3-(4-{2-[3-(2,4-dimethoxyphenyl)-1-heptylureido]ethoxy}phenyl)-2-ethoxypropionic Acid

HRID 1744461Notes

Reaction equation

HRID 1744461 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)C.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1[N:38]=[C:39]=[O:40]>C(Cl)Cl>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1[NH:38][C:39](=[O:40])[N:16]([CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([O:24][CH2:25][CH3:26])[C:4]([OH:3])=[O:27])=[CH:12][CH:11]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 6016372,4-Dimethoxyphenyl isocyanateHCID 696257582-Ethoxy-3-[4-(2-heptylaminoethoxy)phenyl]propionic acid ethyl ester

Product 1

HCID 222345363-(4-{2-[3-(2,4-dimethoxyphenyl)-1-heptylureido]ethoxy}phenyl)-2-ethoxypropionic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound obtained in Example 1, Step e (57.3 mg) in methylene chloride (4 ml) was added with 2,4-dimethoxyphenyl isocyanate (54 μl, Aldrich) and stirred for 1 hour. The reaction mixture was added with a polyamine resin (100 mg, prepared by the method described in J. Am. Chem. Soc., 119, 4874–4881, 1997), further stirred for 1 hour and filtered, and the filtrate was concentrated. The resulting residue was dissolved in ethanol (2 ml), added with 1 N aqueous sodium hydroxide (0.2 ml) and stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, added with 1 N hydrochloric acid (0.2 ml) and concentrated. The resulting residue was dissolved in methylene chloride and washed with 1 N hydrochloric acid. The solution was dried and concentrated, and the resulting residue was applied on a silica gel column and eluted with hexane/acetone (2:1, containing 0.1% acetic acid) to obtain the title compound (59 mg).

Workup

  1. customprepared by the method
  2. stirring, 119, 4874–4881, 1997), further stirred for 1 hour
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in ethanol (2 ml)
  6. additionadded with 1 N aqueous sodium hydroxide (0.2 ml)
  7. stirringstirred at 50° C. for 2 hours
  8. additionadded with 1 N hydrochloric acid (0.2 ml)
  9. concentrationconcentrated
  10. dissolutionThe resulting residue was dissolved in methylene chloride
  11. washwashed with 1 N hydrochloric acid
  12. customThe solution was dried
  13. concentrationconcentrated
  14. washeluted with hexane/acetone (2:1, containing 0.1% acetic acid)

Sources & evidence

ORD record
ord-b75071f0c0804a1f8a688e3c8e6a508a
Source dataset
uspto-grants-2006_03
Patent number
US07015345B2

Reaction notes

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