Pyridine → HCID 57719600, compound

HRID 1985383Notes

Reaction equation

HRID 1985383 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[S:30](Cl)(=[O:32])=[O:31].N1C=CC=CC=1>ClCCl>[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[S:30]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:20])[CH3:21])[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 22493983Ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate

Product 1

HCID 57719600HCID 57719600, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 33 mg of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate and 25 mg of 2,4-dichlorobenzenesulfonyl chloride in 0.8 ml of dichloromethane was added 40 μl of pyridine under ice-cooling, and stirring was continued at room temperature for 4 hours. After removing the solvent, to the residue were added 1.0 ml of ethanol and 0.3 ml of 2N aqueous sodium hydroxide, and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with water, and neutralized with 2N hydrochloric acid. The mixture was extracted with ethyl acetate and concentrated. Then, the residue was purified by HPLC using a reverse-phase column by using an elution solvent of water-acetonitrile-trifluoroacetic acid system, to give 2.0 mg of the title compound.

Workup

  1. temperaturecooling
  2. customAfter removing the solvent
  3. additionto the residue were added 1.0 ml of ethanol and 0.3 ml of 2N aqueous sodium hydroxide
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. additionThe reaction solution was diluted with water
  6. extractionThe mixture was extracted with ethyl acetate
  7. concentrationconcentrated
  8. customThen, the residue was purified by HPLC

Sources & evidence

ORD record
ord-7d9bda4636134498833dda90f442efe6
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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