Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 3-chloro-3-oxopropionate | HCID 118931 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methyl (1-aminocyclopropyl)acetate | HCID 45078843 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86629356 | HCID 86629356 | 40.3% |
Reaction Steps
Chlorocarbonyl-acetic acid ethyl ester (2.75 ml; 22.1 mmol) is added dropwise under stirring and cooling to a solution of (1-amino-cyclopropyl)-acetic acid methyl ester (Chemstep Product List, 13926) (3.00 g; 23.2 mmol) in triethylamine (6.4 ml; 46.2 mmol) and CH2Cl2 (150 ml). After stirring at room temperature for 30 minutes, the reaction mixture is poured on a saturated solution of NaHCO3 and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness. Purification via chromatography (SiO2; hexane/acetone 6:4) yield the title compound as crystalline light-yellow solid (1.9 g; 34%) 1H-NMR (400 MHz; DMSO-d6): 8.40 (s, 1H); 4.07 (q, 2H); 3.60 (s, 3H); 3.12 (s, 2H); 2.58 (s, 2H); 1.17 (t, 3H); 0.71 (m, 2H); 0.66 (m, 2H). MS (m/z) ES+: 244 (MH+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07838674B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-70cf1596e7df4a9a8703d269cb378c29 |
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| Source note | uspto-grants-2010_11 |
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