Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (Naphthalen-2-yl)boronic acid | HCID 2734375 | — |
| Reactant | Dibenzyl[(3,5-dichloro-phenylsulphonylamino)-methyl]-phosphonate | HCID 59534005 | — |
| Catalyst | copper II-acetate | HCID 131711869 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59534044 | HCID 59534044 | — |
Reaction Steps
89 mg 2-naphthaleneboronic acid are added to a mixture of 130 mg dibenzyl [(3,5-dichloro-phenylsulphonylamino)-methyl]-phosphonate and 100 mg molecular sieve (4 Å) in 8 ml of tetrahydrofuran. Then 47 mg copper-II-acetate and 72 μl triethylamine are added and the reaction mixture is stirred for 24 hours at ambient temperature. For working up the reaction mixture is filtered. The filter cake is washed with tetrahydrofuran and the filtrate is evaporated down in vacuo. The flask residue is divided between concentrated aqueous ammonia solution and methylene chloride. The aqueous phase is extracted with methylene chloride and the combined organic phases are washed with 1 N sodium hydroxide solution, dried on magnesium sulphate and evaporated down. The crude product is purified by chromatography through a silica gel column.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163911B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-4ed4bcad16bd43b3a42eaf5d1bad426d |
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| Source note | uspto-grants-2012_04 |
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