HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 551520Generated: October 25, 2026
Dichloromethane → (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide
https://huagongshe.com/reaction/551520
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| Reactant | Bimatoprost | HCID 5311027 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide | HCID 35028392 | 63.5% |
Reaction Steps
A mixture of bimatoprost 1 (0.33 g, 0.8 mmol), DDQ (0.68 g, 3.0 mmol), CH2Cl2 (5 mL) and 1,4-dioxane (5 mL) was stirred for 24 h at 40° C. and evaporated in vacuo. The residue was purified by chromatography on a silica gel (20 g, eluent EtOAc then EtOAc/MeOH 20:1) to give 0.21 g (63%) of 15-keto bimatoprost 1c as yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07947740B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-741db9fb96e34b7a8564348d6d1a63f4 |
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| Source note | uspto-grants-2011_05 |
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