Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Benzenesulfonyl hydrazide | HCID 65723 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 4-{[(Tert-butoxy)carbonyl]amino}benzoic acid | HCID 2755931 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 15885492 | HCID 15885492 | — |
Reaction Steps
12.1 mmol (1.65 g) of 1-hydroxy-7-azabenzotriazole and 18 mmol (3.45 g) of EDCI are added in succession to a solution of 12 mmol (2.85 g) of 4-[(tert-butoxycarbonyl)amino]benzoic acid in 20 ml of dimethylformamide. The reaction mixture is stirred at room temperature for one hour, and 18 mmol (3.1 g) of benzenesulphonohydrazide are added. After stirring for eight hours at room temperature, the reaction mixture is poured into 100 ml of a 10% hydrochloric acid solution and extracted four times with 50 ml of ethyl acetate. The organic phase is washed twice with 50 ml of water and then three times with an aqueous saturated sodium hydrogen carbonate solution and once with 50 ml of an aqueous saturated sodium chloride solution. After drying over magnesium sulphate, filtration and concentration, the expected product is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06596749B2 |
|---|
| Source dataset | uspto-grants-2003_07 |
|---|
| ORD ID | ord-73267cd14e75470a80779e6dae86c9a2 |
|---|
| Source note | uspto-grants-2003_07 |
|---|