Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | HCID 22841465 | HCID 22841465 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22841466 | HCID 22841466 | 81.6% |
Reaction Steps
A mixture of 2-[2-(-(S)-4-benzyloxycarbonylamino-4-carboxybutanamido)ethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (1.0 g), ethanol (0.27 g), N,N'-dicyclohexylcarbodiimide ("DCCD") (0.34 g) and 4-dimethylaminopyridine (50 mg) was stirred in dichloromethane (10 ml) at room temperature for 18 hours. The resulting N,N'-dicyclohexylurea was then removed by filtration and the filtrate evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0→2% methanol as the eluant. Appropriate fractions were combined and evaporated to give 2-[2-(-(S)-4-benzyloxycarbonylamino-4-ethoxycarbonylbutanamido)ethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (0.85 g) as an essentially pure oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04806557 |
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| Source dataset | uspto-grants-1989_02 |
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| ORD ID | ord-9a248e37e96b46c28c28cfcab40ff02d |
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| Source note | uspto-grants-1989_02 |
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