HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetoacetic Acid → (3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetoacetic Acid | HCID 96 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | (3S)-2-oxo-3-benzoylamino-5-acetoacetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester | HCID 57080557 | — |
| Reactant | HCID 57313411 | HCID 57313411 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester | HCID 57159598 | — |
Reaction Steps
Method B. (3S)-2-oxo-3-benzoylamino-5-acetoacetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester (602g). A 0° C. solution of (3S)-2-oxo-3-(benzoylamino)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester (600b) (465 mg, 1.10 mmol) in CH2Cl2 (5 ml) was treated with acetoacetic acid in 1 ml of CH2Cl2 followed by slow addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (431 mg, 2.2 mmol) in 2 ml of CH2Cl2 under N2 atmosphere. After 15 min the reaction was poured onto EtOAc, washed with aq. 5% NaHSO4, dried over Na2SO4 and concentrated in vacuo.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08119631B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-2b90de2cd0814da4b103e29798e5e1b5 |
| Source note | uspto-grants-2012_02 |