HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1917362Generated: November 1, 2026
Lawesson's reagent → [(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/1917362
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | [(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester | HCID 67490826 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | [(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester | HCID 86664651 | 133.3% |
Reaction Steps
[(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester (88.0 mg, 0.27 mmol) was dissolved in toluene (8 mL). Lawesson's reagent (81.5 mg, 0.20 mmol) was added, and the mixture was stirred at 80° C. for four hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 91.6 mg of the title compound as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618094B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-c7d40dc8d0af4630a121af87fe3070f0 |
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| Source note | uspto-grants-2013_12 |
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