HuagongsheHuagongshe Chemistry Print Report · For research reference only
Succinamic acid → (5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(3-carbamoylpropionyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Succinamic acid | HCID 12522 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione | HCID 11281440 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(3-carbamoylpropionyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dione | HCID 10239341 | 70.3% |
Reaction Steps
A mixture of (5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione (82.7 mg), succinamic acid (45.86 mg), EDC (93.12 mg), HOBT (61.24 mg) and DIEA (104.79 μL) in THF (5 mL) was stirred overnight at room temperature. The reaction mixture was concentrated and purified by high performance liquid chromatography (HPLC) (Beckman 5μ C18 column; eluted with a gradient of H2O/MeCN (10-100%)/0.1% TFA) to give 72 mg of the titled compound. MS (m/z) 536 (MNa+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07375128B2 |
| Source dataset | uspto-grants-2008_05 |
| ORD ID | ord-dbd7c1e47bb64ee990132b77bc035511 |
| Source note | uspto-grants-2008_05 |