Sodium Hydroxide → HCID 135610110, compound

HRID 733381Notes

Reaction equation

HRID 733381 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[C:8]([S:10]([N:13]([CH2:32][C:33]2[N:34]=[C:35]([CH3:38])[S:36][CH:37]=2)[CH2:14][CH2:15][C:16]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][C:17]=2[O:18][CH2:19][C:20]([O:22]CC)=[O:21])(=[O:12])=[O:11])[CH:9]=1)(=[NH:3])[NH2:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[C:8]([S:10]([N:13]([CH2:32][C:33]2[N:34]=[C:35]([CH3:38])[S:36][CH:37]=2)[CH2:14][CH2:15][C:16]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:30])[CH3:31])=[CH:25][C:17]=2[O:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:11])=[O:12])[CH:9]=1)(=[NH:2])[NH2:3]

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-isopropyl-phenoxy]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-1f8ecb4a0f34467e84cbf630aa17d273
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

Loading…