Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 3-chloro-3-oxopropionate | HCID 118931 | — |
| Reactant | 546114-00-5 | HCID 11332703 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59558423 | HCID 59558423 | 82.2% |
Reaction Steps
Chlorocarbonyl-acetic acid ethyl ester (1.24 ml; 11.2 mmol) in CH2Cl2 (5 ml) is added dropwise under stirring within 15 minutes at room temperature to a solution of 1′-amino-bicyclopropyl-1-carboxylic acid ethyl ester (1.38 g; 8.16 mmol) (Synlett. 2003, 2, 265) and triethylamine (1.02 ml; 10.4 mmol) in CH2Cl2 (100 ml). Stirring is continued for 5 minutes, then the reaction mixture is poured on water, acidified with 2N HCl and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness. The combined organic phases are dried over Na2SO4, filtered, evaporated and purified via chromatography (SiO2; acetone/heptane 9:92>2/8) to yield the title compound as off-white crystals (1.9 g; 79%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07838674B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-cde24668f26046afb8407c1461c1c709 |
|---|
| Source note | uspto-grants-2010_11 |
|---|