Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Homoserine lactone hydrobromide | HCID 73508 | — |
| Reactant | 4-Phenoxybenzene-1-sulfonyl chloride | HCID 2794756 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 18753497 | HCID 18753497 | 73% |
Reaction Steps
Triethylamine (20.0 ml, 143.9 mmol) was added to a suspension of α-amino-γ-butyrolactone hydrobromide (7.28 g, 40.0 mmol) in dichloromethane (80 ml), and then 20 minutes were spent in adding dropwise a solution of 4-phenoxybenzenesulfonyl chloride (11.0 g, 40.9 mmol) in dichloromethane (40 ml) to the mixture with ice-cooling. After this mixture was stirred at room temperature for 2 hours, the solvent of the reaction mixture was evaporated under reduced pressure. The residue was acidified with water and hydrochloric acid (1N), and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as the eluant to give the title compound (8.74 g, yield 73%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06673804B1 |
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| Source dataset | uspto-grants-2004_01 |
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| ORD ID | ord-fb2d5ccdde504e69a02f2942a317ac65 |
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| Source note | uspto-grants-2004_01 |
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