HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → HCID 66935020, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bis-(1H-imidazol-2-YL)-methanone | HCID 5250894 | — |
| Reactant | HCID 66934929 | HCID 66934929 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66935020 | HCID 66935020 | 90% |
Reaction Steps
To a solution of (2R)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propionic acid (1.1 g, 98% ee) in tetrahydrofuran (32 ml), carbonyl diimidazole (600 mg) was added under ice cooling and the mixture was stirred at room temperature for 1 hour 20 minutes. To the reaction solution, methanol (12.5 ml) and triethylamine (4.3 ml) were added and the mixture was stirred at room temperature for 3 hours. To the reaction solution, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then solvent was distilled off in vacuo. The obtained residue was purified by silica gel column chromatography to obtain the title compound (1.03 g, 98%ee) as an oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08049006B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-0465f7054c1e4e978386379d3d3f3b12 |
| Source note | uspto-grants-2011_11 |