Hydrochloric Acid → 5-cyano-N-[2-(3-hydroxy-2'-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

HRID 733360Notes

Reaction equation

HRID 733360 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:35][CH3:36])=[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[O:31]COC)(=[O:11])=[O:10])[CH:8]=1)#[N:2].Cl>C(O)(C)C.O1CCCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:35][CH3:36])=[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[OH:31])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 178562285-cyano-N-[2-(2'-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

Product 1

HCID 178562275-cyano-N-[2-(3-hydroxy-2'-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamideYield 74.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 14.89 g of 5-cyano-N-[2-(2′-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-meth oxybenzenesulfonamide in a mixture of 30 mL of isopropanol and 90 mL of tetrahydrofuran was added 11.7 mL of concentrated hydrochloric acid. After being stirred at 50° C. for 2 hours, the reaction mixture was diluted with 50 mL of water, and extracted with 150 mL of ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, 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-methanol) to give 10.22 g of 5-cyano-N-[2-(3-hydroxy-2′-methanesulfonylbiphenyl-4-yl)ethyl]-2-Methoxybenzenesulfonamide, colorless and amorphous.

Workup

  1. extractionextracted with 150 mL of ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, 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-methanol)

Sources & evidence

ORD record
ord-fc4000476261471a9ad60ba1ba8acc1f
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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