HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoromethanesulfonic acid → benzyloxycarbonyl-beta-(allylamino)-L-alanine, methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoromethanesulfonic acid | HCID 62406 | — |
| Reactant | Allyl 2,2,2-Trichloroacetimidate | HCID 316905 | — |
| Reactant | 3-Amino-N-((phenylmethoxy)carbonyl)-L-alanine methyl ester | HCID 11043221 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Dichloromethane cyclohexane | HCID 21916607 | — |
| Product | benzyloxycarbonyl-beta-(allylamino)-L-alanine, methyl ester | HCID 131719024 | — |
Reaction Steps
Dissolve Nα -(benzyloxycarbonyl)-β-(amino)-L-alanine, methyl ester (15.9g, 63mmol) in methylene chloride/cyclohexane (1:1, 600mL). Add allyl trichloroacetimidate (26g, 128mmol) and trifluoromethanesulfonic acid (5mL), 56.6mmol). Stir at room temperature under a nitrogen atmosphere for 5 hours and dilute with methylene chloride. Wash with saturated aqueous sodium hydrogen carbonate, water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give Nα -(benzyloxycarbonyl)-β-(allylamino)-L-alanine, methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05430145 |
| Source dataset | uspto-grants-1995_07 |
| ORD ID | ord-dcd61288683a4ec5974ad2b502307789 |
| Source note | uspto-grants-1995_07 |