Hydrochloric Acid → Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

HRID 853955Notes

Reaction equation

HRID 853955 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([CH3:38])(=[O:37])=[O:36])[CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:20]=1[O:27]C)(=[O:18])=[O:17])[CH3:2].[Cl-].[Li+].C(OCC)(=O)C.Cl>CN(C)C=O.C1(C)C=CC=CC=1>[C:25]([C:23]1[CH:22]=[CH:21][C:20]([OH:27])=[C:19]([S:16]([NH:15][CH2:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35]([CH3:38])(=[O:37])=[O:36])=[CH:8][C:7]=2[O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:39])(=[O:17])=[O:18])[CH:24]=1)#[N:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 10393283Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

Product 1

HCID 12149205Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetateYield 81.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4.62 g of ethyl[4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2′-methanesulfonyl biphenyl-3-yloxy]acetate in 40 mL of N,N-dimethylformamide was added 1.03 g of lithium chloride, and the mixture was stirred at 140° C. for 2 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of 60 mL of ethyl acetate, 6 mL of toluene, and 32 mL of 1 mol/L hydrochloric acid. The organic layer was separated, and washed with 1 mol/L hydrochloric acid and brine. The organic layer was 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: acetic acid-ethyl acetate) to give 3.67 g of ethyl [4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate as a colorless amorphous.

Workup

  1. temperatureAfter being cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with 1 mol/L hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: acetic acid-ethyl acetate)

Sources & evidence

ORD record
ord-d16587580744451fac4c23a551e5415d
Source dataset
uspto-grants-2007_08
Patent number
US07256215B2

Reaction notes

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