Sodium Hydroxide → HCID 135610110, compound

HRID 229611Notes

Reaction equation

HRID 229611 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17][N:18]([S:26]([C:29]1[CH:34]=[C:33]([C:35](=[NH:37])[NH2:36])[CH:32]=[CH:31][C:30]=1[OH:38])(=[O:28])=[O:27])[CH2:19][C:20]1[N:21]=[C:22]([CH3:25])[S:23][CH:24]=1)C.[OH-].[Na+]>C(O)C>[C:35]([C:33]1[CH:32]=[CH:31][C:30]([OH:38])=[C:29]([S:26]([N:18]([CH2:19][C:20]2[N:21]=[C:22]([CH3:25])[S:23][CH:24]=2)[CH2:17][CH2:16][C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:14])[CH3:15])=[CH:12][C:7]=2[O:6][CH2:5][C:4]([OH:39])=[O:3])(=[O:27])=[O:28])[CH:34]=1)(=[NH:36])[NH2:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136375596HCID 136375596, compound

Product 1

HCID 135610110HCID 135610110, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 100 mg of ethyl[2-[2-[(5-carbamimidoyl-2-hydroxybenzenesulfonyl)-(2-methyl-1,3-thiazol-4-ylmethyl)amino]ethyl]-5-isopropylphenoxy]acetate in 0.8 mL of ethanol was added 0.183 mL of 2 mol/L sodium hydroxide solution under ice-cooling. After being stirred at the same temperature for 30 minutes, the reaction mixture was concentrated under reduced pressure. To the stirred solution of the residue in a mixture of 0.8 mL of acetonitrile and 0.8 mL of water was added 0.174 mL of 1 mol/L hydrochloric acid under ice-cooling, and the mixture was stirred at the same temperature for 5 minutes. To the mixture was added additional 0.174 mL of 1 mol/L hydrochloric acid under ice-cooling, and the mixture was stirred at the same temperature for 5 minutes. The precipitate was collected by filtration, and washed with water to give 74 mg of [2-[2-[(5-carbamimidoyl-2-hydroxybenzenesulfonyl)-(2-methyl-1,3-thiazole-4-ylmethyl)amino]ethyl]-5-isopropylphenoxy]acetic acid.

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the stirred solution of the residue in a mixture of 0.8 mL of acetonitrile and 0.8 mL of water
  4. additionwas added 0.174 mL of 1 mol/L hydrochloric acid under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred at the same temperature for 5 minutes
  7. additionTo the mixture was added additional 0.174 mL of 1 mol/L hydrochloric acid under ice-
  8. temperaturecooling
  9. stirringthe mixture was stirred at the same temperature for 5 minutes
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with water

Sources & evidence

ORD record
ord-5e5a3c5fd27e436f8bd398128f97bf67
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Reaction notes

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