HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → Methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methyl 4-[(methylamino)methyl]benzoate | HCID 11194668 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate | HCID 66621459 | 53.5% |
Reaction Steps
Methyl 4-((methylamino)methyl)benzoate was dissolved in the mixed solution of THF (12 mL) and water (12 mL), then benzyl carbonochloridate (2.57 g, 15.0 mmol) was dropped into it. To the mixture sodium bicarbonate (1.7 g, 20.5 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was poured into ethyl acetate (50 mL×3) and the organic layer was washed with saturated sodium bicarbonate solution, dried with anhydrous sodium sulfate and condensed to get methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate (2.3 g, 53.5%), LC-MS (ESI) m/z 314 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08088760B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-c9fb1985447b494fa67939d1be3e1ff2 |
| Source note | uspto-grants-2012_01 |