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HRID 464462Erstellt: 24. Oktober 2026
Dicyclohexylcarbodiimide → (S)alpha-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-[2-(cyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylate
https://huagongshe.com/de/reaction/464462
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
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| Edukt | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Edukt | (2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile | HCID 9837437 | — |
| Edukt | (1R,cis)2,2-dimethyl-3-[2-cyclopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylic acid | HCID 18599577 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | (S)alpha-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-[2-(cyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylate | HCID 131714381 | 68,4% |
Reaktionsschritte
2.96 g of dicyclohexylcarbodiimide were added at 0° C. to a stirred mixture of 3.6 g of the product of Step B, 30 ml of methylene chloride and 30 mg of 4-dimethylaminopyridine followed by the addition of a solution of 3.3 g of (S)α-cyano-3-phenoxy-benzyl alcohol in 10 ml of methylene chloride. The mixture was stirred at 0° C. for 5 minutes and at 20°-25° C. for 3 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a cyclohexane-ethyl acetate mixture yielded 4.5 g of (S)α-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-[2-(cyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylate with a melting point of =72° C.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US04547522 |
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| Quelldatensatz | uspto-grants-1985_10 |
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| ORD ID | ord-35cc5308e291490b9e64da0d0b9a6f79 |
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| Quellennotiz | uspto-grants-1985_10 |
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