Pyridine → 3-[3-(2,4-Dichlorobenzyloxycarbonylamino)-4-methoxyphenyl]-2-isopropoxypropanoic acid

HRID 1985412Notes

Reaction equation

HRID 1985412 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH2:12][CH:13]([O:19][CH:20]([CH3:22])[CH3:21])[C:14]([O:16]CC)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])=[C:2]=[O:3].[Cl:23][C:24]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=1[CH2:26][OH:27].N1C=CC=CC=1>O1CCCC1>[Cl:23][C:24]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=1[CH2:26][O:27][C:2]([NH:1][C:4]1[CH:5]=[C:6]([CH2:12][CH:13]([O:19][CH:20]([CH3:21])[CH3:22])[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 156842,4-Dichlorobenzyl alcoholHCID 22927009Ethyl 3-(3-isocyanato-4-methoxyphenyl)-2-isopropoxypropanoate

Product 1

HCID 577195653-[3-(2,4-Dichlorobenzyloxycarbonylamino)-4-methoxyphenyl]-2-isopropoxypropanoic acidYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14 mg of Ethyl 3-(3-isocyanato-4-methoxyphenyl)-2-isopropoxypropanoate was dissolved in 1 ml of tetrahydrofuran, and 10 mg of 2,4-dichlorobenzyl alcohol and 5 μl of pyridine were added thereto, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under a stream of nitrogen, and the residue was dissolved in 0.6 ml of ethanol, and 0.12 ml of 5N sodium hydroxide was added and stirred at room temperature for 1 hour. The reaction solution was diluted with 1 ml of water and 0.14 ml of 5N hydrochloric acid, and extracted with ethyl acetate. The organic layer was collected, and the solvent was removed under a stream of nitrogen. The residue was purified by HPLC using a reverse-phase column and a water-acetonitrile-trifluoroacetic acid elution solvent, to give 3.1 mg of the title compound.

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. dissolutionthe residue was dissolved in 0.6 ml of ethanol
  3. addition0.12 ml of 5N sodium hydroxide was added
  4. stirringstirred at room temperature for 1 hour
  5. additionThe reaction solution was diluted with 1 ml of water and 0.14 ml of 5N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was collected
  8. customthe solvent was removed under a stream of nitrogen
  9. customThe residue was purified by HPLC
  10. washa water-acetonitrile-trifluoroacetic acid elution solvent

Sources & evidence

ORD record
ord-ca6a1220b06d4e0cbbe7dce75069b523
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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