Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Chlorosulfonyl isocyanate | HCID 70918 | — |
| Reactant | benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate | HCID 12834624 | — |
| Reactant | HCID 15706331 | HCID 15706331 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86742708 | HCID 86742708 | — |
Reaction Steps
To a suspension of 1.10 g of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (5.0 mmol) in 40 ml of dry ethyl acetate, 0.45 ml (5.0 mmol) of chlorosulfonyl isocyanate was added with stirring. The mixture was stirred for 1 hour at room temperature and then cooled to 0° C. After the dropwise addition of a solution of 2.09 ml (15.0 mmol) of triethylamine in 10 ml of dry dichloromethane and solution A, stirring was continued for 2.5 hours at 0° C. Ice water was added, and the organic layer was separated and washed successively with cold buffer solution (citrate pH 2) and brine. Drying (magnesium sulfate) and evaporation in vacuo gave a residue which solidified by stirring with ether; yield: 2.1 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04801705 |
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| Source dataset | uspto-grants-1989_01 |
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| ORD ID | ord-4585be04351c4709915427243d6cc656 |
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| Source note | uspto-grants-1989_01 |
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