Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Acetohydrazide | HCID 14039 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | N-((1,1-dimethylethoxy)carbonyl)-beta-alanine | HCID 76809 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 9992082 | HCID 9992082 | — |
Reaction Steps
EDCI.HCl (3.05 g, 15.95 mmol), HOBt (1.66 g, 12.27 mmol) and triethylamine (2.22 ml, 15.95 mmol) are added to a stirred solution of BOC-β-Ala-OH (2.32 g, 12.27 mmol) in DCM (60 ml). After stirring for 30 min at 0° C. acetic acid hydrazide (1.0 g, 13.5 mmol) is added in one portion. The reaction mixture is stirred at 0° C. for 1 hour. The reaction is diluted with water and extracted several times with DCM. The organic extract is dried (MgSO4) and the solvent is removed to give an oil. Purification by chromatography on silica, eluting with EtOAc increasing to EtOAc:EtOH 10:1, affords the titled compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07902375B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-29e64feb3c504841bab2d3d246281422 |
|---|
| Source note | uspto-grants-2011_03 |
|---|
