Water → Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

HRID 733361Notes

Reaction equation

HRID 733361 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:32][CH3:33])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:17][C:16]=2[OH:31])(=[O:11])=[O:10])[CH:8]=1)#[N:2].C(N(CC)C(C)C)(C)C.Br[CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46].O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:32][CH3:33])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([CH3:30])(=[O:28])=[O:29])=[CH:17][C:16]=2[O:31][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 178562275-cyano-N-[2-(3-hydroxy-2'-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

Product 1

HCID 10393283Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5.72 g of 5-cyano-N-[2-(3-hydroxy-2′-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide in 57 mL of N,N-dimethylformamide were added 2.46 mL of N,N-diisopropylethylamine and 1.37 mL of ethyl bromoacetate. After being stirred at 50° C. for 15 hours, and the reaction mixture was poured into 100 mL of water, and extracted with a mixture of 150 mL of ethyl acetate and 20 mL of toluene. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate-hexane) to give 2.96 g of ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate, amorphous.

Workup

  1. extractionextracted with a mixture of 150 mL of ethyl acetate and 20 mL of toluene
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a1ff70530b5b4707b6fde6c010595bb5
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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