Hydrochloric Acid → HCID 135456120, compound

HRID 733374Notes

Reaction equation

HRID 733374 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[C:8]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([CH3:31])(=[O:30])=[O:29])=[CH:18][C:17]=2[O:32][CH2:33][C:34]([O:36]CC)=[O:35])(=[O:12])=[O:11])[CH:9]=1)(=[NH:3])[NH2:2].[OH-].[Na+].[ClH:42]>C(#N)C>[ClH:42].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[C:8]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([CH3:31])(=[O:30])=[O:29])=[CH:18][C:17]=2[O:32][CH2:33][C:34]([OH:36])=[O:35])(=[O:11])=[O:12])[CH:9]=1)(=[NH:2])[NH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 136367330HCID 136367330, compound

Product 1

HCID 135456120HCID 135456120, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 290 mg of ethyl [4-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonoyl-biphenyl-3-yloxy]acetate in 1.0 mL of acetonitrile was added 0.756 mL of 2 mol/L sodium hydroxide solution, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 1.26 mL of 2 mol/L hydrochloric acid, and the mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was purified by column chromatography on trimethylaminopropylated silica gel (eluent: 10% 1 mol/L hydrochloric acid-acetonitrile). The eluent was concentrated under reduced pressure to give 260 mg of [4-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)-ethyl]-2′-methanesulfonoylbiphenyl-3-yloxy]acetic acid hydrochloride as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. customthe mixture was purified by column chromatography on trimethylaminopropylated silica gel (eluent: 10% 1 mol/L hydrochloric acid-acetonitrile)
  4. concentrationThe eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-92a5d0342137402e93dc3f63962395bd
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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