HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (5-Chloro-2-[(E)-3-[(2S,5R)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl]-3-oxopropenyl]-phenyl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-(2-{[(Tert-butoxy)carbonyl]amino}-4-chlorophenyl)prop-2-enoic acid | HCID 11630775 | — |
| Reactant | (2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine | HCID 23405839 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (5-Chloro-2-[(E)-3-[(2S,5R)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl]-3-oxopropenyl]-phenyl)-carbamic acid tert-butyl ester | HCID 58683713 | 83.7% |
Reaction Steps
(E)-3-(2-tert-Butoxycarbonylamino-4-chlorophenyl)-acrylic acid (595 mg, 2.0 mmol) and (2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine (Mavunkel, Babu J. et al., WO 00/71535) (445 mg, 2.0 mmol) were dissolved in CH2Cl2, combined with EDCl.HCl (384 mg, 2.0 mmol) and stirred for 3 hours at room temperature. The reaction mixture was purified via chromatography (SiO2, EtOAc/hexanes 2/8) to yield the title compound as colorless foam (840 mg, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07645760B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-e7e5051fbc204abeafe0f8666c3d737e |
| Source note | uspto-grants-2010_01 |