HCID 136375592, compound → HCID 135610111, compound

HRID 1351799Notes

Reaction equation

C([O:3][C:4](=[O:32])[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][NH:18][S:19]([C:22]1[CH:27]=[C:26]([C:28](=[NH:30])[NH2:29])[CH:25]=[CH:24][C:23]=1[OH:31])(=[O:21])=[O:20])C>Cl.C(#N)C>[C:28]([C:26]1[CH:25]=[CH:24][C:23]([OH:31])=[C:22]([S:19]([NH:18][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:32])=[O:3])(=[O:20])=[O:21])[CH:27]=1)(=[NH:29])[NH2:30]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl[2-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate (50 mg) was dissolved in a mixture of 3 mL of 1 mol/L hydrochloric acid and 1 mL of acetonitrile at 60° C. The solution was stirred at 60° C. for 4 hours, and the colorless solid obtained by concentration under reduced pressure of the reaction mixture was dissolved in a mixture of 3 mL of 1 mol/L hydrochloric acid and 1 mL of acetnitrile at 60° C. After the solution was stirred at 60° C. for 4 hours, then at room temperature for 10 hours, the reaction mixture was concentrated under reduced pressure to give a colorless solid. The solid was triturated with water and diethyl ether, and collected by filtration to give 31 mg of [2-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid.

Workup

customthe colorless solid obtained by concentration under reduced pressure of the reaction mixture
stirringAfter the solution was stirred at 60° C. for 4 hours
waitat room temperature for 10 hours
concentrationthe reaction mixture was concentrated under reduced pressure
customto give a colorless solid
customThe solid was triturated with water and diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-f0e4e207102b4ee68ac85f7505831704
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217832B2

Reaction notes

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