HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → HCID 86701052, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | tert-butyl 3-hydrazinyl-3-oxopropylcarbaMate | HCID 50998849 | — |
| Reactant | (2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid | HCID 57389355 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 86701052 | HCID 86701052 | 53.3% |
Reaction Steps
To a solution of the carboxylic acid (6b, 390 mg, 1.41 mmol) of Example 9 or 16 in methylene chloride (14.1 mL) were added triethylamine (393 μl), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (406 mg), 1-hydroxybenzotriazole.monohydrate (324.6 mg), and tert-butyl(3-hydrazinyl-3-oxopropyl)carbamate (430.8 mg, prepared following a procedure analogous to Reference Example 2), followed by agitating at room temperature overnight. The reaction solution was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (ethyl acetate) to afford 347.3 mg of the title compound (yield 53.3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181250B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-fadd6c8177d745a2b2b03dd9bebec34b |
| Source note | uspto-grants-2015_11 |