Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Proline benzyl ester hydrochloride | HCID 2733413 | — |
| Reactant | HCID 67554200 | HCID 67554200 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86754247 | HCID 86754247 | 22.3% |
Reaction Steps
To solution of sodium 2-(7-oxo-4-oxa-1-azabicyclo [3,2,0] heptan-3-yl)-acetate (194 mg, 1 mmol) in 2 ml of DMSO and 10 ml of dichloromethane, ethyl chloroformate (109 mg, 1 mmol) was added at -15° C. After stirring at -15° C. for 30 mins, a precooled (ca. -10° C.) solution of L-proline benzyl ester hydrochloride (242 mg, 1 mmol), triethylamine (110 mg, 1.1 mmol) in chloroform (8 ml) was added at -10° C. The resulting mixture was stirred at -10 to 0° C. for 2 hrs and at room temperature overnight, and then diluted with chloroform, washed with water, dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:2) as eluent and 80 mg of the title compound was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05925633 |
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| Source dataset | uspto-grants-1999_07 |
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| ORD ID | ord-aa034d6665ef45d08c50f362d4641444 |
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| Source note | uspto-grants-1999_07 |
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