HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → N-benzyloxy-N-[(R)-2-(N'-pyridin-2-yl-hydrazinocarbonyl)-heptyl]-formamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 2-Hydrazinopyridine | HCID 78645 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | (2R)-[(benzyloxyformylamino)methyl]heptanoic acid | HCID 66603339 | — |
| Product | N-benzyloxy-N-[(R)-2-(N'-pyridin-2-yl-hydrazinocarbonyl)-heptyl]-formamide | HCID 86600960 | — |
Reaction Steps
(2R)-[(benzyloxyformylamino)methyl]heptanoic acid (1.2 mmoles), HOAt (1.3 mmoles), N′-pyridin-2-yl-hydrazine (1.2 mmoles) and NMM (5 mmoles) were dissolved in DMF and treated with EDCI (1.3 mmoles) at room temperature for 12 hours. The coupling product N-benzyloxy-N-[(R)-2-(N′-pyridin-2-yl-hydrazinocarbonyl)-heptyl]-formamide was isolated by prep hplc of the crude reaction mixture. This compound was submitted to atmospheric pressure hydrogenation over Pd/C in methanol for 1 hour, yielding the title compound. MH+295.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07919528B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-61d1cb24bf49496bb5340013bea9c567 |
| Source note | uspto-grants-2011_04 |