(2,4-Dichlorophenoxy)Acetic Acid → 3-{3-[2-(2,4-Dichlorophenoxy)acetylamino]-4-methoxyphenyl}-2-isopropoxypropanoic acid

HRID 1985407Notes

Reaction equation

HRID 1985407 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14]CC)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:21][C:22]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:23]=1[O:24][CH2:25][C:26](O)=[O:27].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C>O1CCCC1>[Cl:21][C:22]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:23]=1[O:24][CH2:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([O:17][CH:18]([CH3:19])[CH3:20])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])=[O:27]

Participants

6

Reactant 4

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22494286Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate

Product 1

HCID 577195233-{3-[2-(2,4-Dichlorophenoxy)acetylamino]-4-methoxyphenyl}-2-isopropoxypropanoic acidYield 8.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

30 mg of Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate and 20 mg of 2,4-dichlorophenoxyacetic acid were dissolved in 0.5 ml of tetrahydrofuran, and 30 mg of carbonyldiimidazole and 0.05 ml of triethylamine were added, and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was then partitioned between water and ethyl acetate, and the organic layer was concentrated. The residue was dissolved in 0.6 ml of ethanol, and 0.12 ml of 5N sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was neutralized with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by HPLC using a reverse-phase column and a water-acetonitrile-trifluoroacetic acid elution solvent, to give 3.4 mg of the title compound.

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. dissolutionThe residue was dissolved in 0.6 ml of ethanol
  4. addition0.12 ml of 5N sodium hydroxide was added
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. extractionextracted with ethyl acetate
  7. concentrationThe organic layer was concentrated
  8. customthe residue was purified by HPLC
  9. washa water-acetonitrile-trifluoroacetic acid elution solvent

Sources & evidence

ORD record
ord-732e35fd889f415092ab96ba38c09a7f
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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