HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → benzyl N-[(6S,8R)-8-azido-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (6S,8R)-3-(allyl-benzyloxycarbonyl-amino)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid | HCID 86590672 | — |
| Reactant | N-Cbz-4-(aminomethyl)benzamidine | HCID 138391585 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | benzyl N-[(6S,8R)-8-azido-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate | HCID 145857216 | 90% |
Reaction Steps
To a solution of 18f (270 mg, 0.636 mmol) and [(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester (272 mg, 0.763 mmol) in 6 mL CH2Cl2/DMF (5:1) at 0° C., were added HOAT (95 mg, 0.700 mmol), NaHCO3 (187 mg, 2.23 mmol), and EDCI (171 mg, 0.890 mmol). The mixture was allowed to warm to rt and stir for 15 h. The mixture was diluted with EtOAc, washed with H2O, 1 N HCl, H2O, sat. NaHCO3, and brine. The mixture was dried (Na2SO4) and concentrated to afford 393 mg (90%) of intermediate 18 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07094783B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-4d03171be84a4409a5d812f09daa32c8 |
| Source note | uspto-grants-2006_08 |