Methanol → HCID 69628825, compound

HRID 987310Notes

Reaction equation

HRID 987310 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[C:35]([Cl:39])=[CH:34][C:33]=1[S:40](Cl)(=[O:42])=[O:41].CO>C(#N)C.ClCCl>[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[C:35]([Cl:39])=[CH:34][C:33]=1[S:40]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:7][CH:8]=1)(=[O:42])=[O:41]

Participants

7

Reactant 4

HCID 887MethanolHCID 275752,4,5-Trichlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86595065HCID 86595065, compound

Product 1

HCID 69628825HCID 69628825, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (described in Example 56a) (0.2 g; 0.547 mmole) and sodium hydrogen carbonate (0.05 g; 0.6 mmole) were mixed in acetonitrile (10 ml) and stirred at room temperature for 15 minutes. The mixture was then cooled in an ice-bath and 2,4,5-trichlorobenzenesulfonyl chloride (0.184 g; 0.657 mmole) was added. After addition, the ice-bath was removed and the reaction mixture was heated to reflux for 4 hours and then evaporated to dryness. Ethyl acetate and water were added to the residue and the phases were separated. The organic phase was dried with magnesium sulfate and the solvent was evaporated. Chromatography on silica gel (Isolute, SI) using dichloromethane and then methanol (2%) in dichloromethane as eluant gave 0.28 g (89% yield) of 3-(4-{2-[4-(2,4,5-trichlorobenzenesulfonylamino)phenyl]ethoxy}phenyl]-(S)-2-ethoxypropanoic acid.

Workup

  1. temperatureThe mixture was then cooled in an ice-bath
  2. additionAfter addition
  3. customthe ice-bath was removed
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for 4 hours
  6. customevaporated to dryness
  7. additionEthyl acetate and water were added to the residue
  8. customthe phases were separated
  9. dry with materialThe organic phase was dried with magnesium sulfate
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-69eca945aeb2412ba1503721d4b88e6c
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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