HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → CID 145857197
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (S)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic Acid | HCID 57444827 | — |
| Reactant | tert-butyl N-[4-(aminomethyl)benzenecarboximidoyl]carbamate | HCID 145832046 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | CID 145857197 | HCID 145857197 | 79.2% |
Reaction Steps
To a solution of intermediate 25a (0.281 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester (84 mg, 0.337 mmol) in 3 mL 5:1 CH2Cl2/DMF at 0° C., were added NaHCO3 (59 mg, 0.703 mmol), HOAT (42.1 mg, 0.309 mmol), and EDCI (75.5 mg, 0.393 mmol). The mixture was allowed to warm to rt and stir 20 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, and sat. NaHCO3, and brine, dried (Na2SO4) and brine. The crude residue was triturated with Et2O to afford 160 mg (79%) of intermediate 25b as a white solid. MS (ESI) 719.4 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07094783B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-f36da15899fd4af9811f6c580396af9c |
| Source note | uspto-grants-2006_08 |