Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroacetone | HCID 6571 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methyl N-benzyl-L-alaninate--hydrogen chloride (1/1) | HCID 45489685 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67092693 | HCID 67092693 | 50% |
Reaction Steps
A mixture of N-benzylalanine methyl ester hydrochloride (1.00 g, 4.35 mmol), chloroacetone (1.21 g, 13.1 mmol), and sodium hydrogencarbonate (951 mg, 11.3 mmol) in 1,4-dioxane (11 mL) and water (1 mL) was heated at 70° C. for 2 days, then partitioned between EtOAc and 2 M aq. sodium carbonate solution. The organic layer was dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (540 mg, 50%). Colourless oil, MS: 250.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08471004B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-876957e2cc434ff89ae46209e44cb790 |
|---|
| Source note | uspto-grants-2013_06 |
|---|
