Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid | HCID 2776400 | — |
| Reactant | HCID 15428308 | HCID 15428308 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 70096722 | HCID 70096722 | 71% |
Reaction Steps
To a solution of 1-benzyloxycarbonyl-2-indoline carboxylic acid (320 mg, 1.05 mmol) and triethylamine (106 mg, 1.05 mmol) in chloroform (20 ml), ethyl chloroformate (109 mg, 1 mmol) was added at -15° C. The reaction mixture was stirred at a bath temperature of -10 to 5° C. for 1 hr. Then a precooled solution of (3S,4S)-3-amino-4-acetoxy-azetidin-2-one in ethyl acetate was added at -15° C. and stirring was continued at a bath temperature of -15 to 5° C. for 1 hr. After removal of solvent, the residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:3) as eluent and the title compound was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05959123 |
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| Source dataset | uspto-grants-1999_09 |
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| ORD ID | ord-dcb480c362444f43a6970770ca97fa55 |
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| Source note | uspto-grants-1999_09 |
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