Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 23388233 | HCID 23388233 | — |
| Catalyst | HCID 23388045 | HCID 23388045 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 23388198 | HCID 23388198 | 78.8% |
Reaction Steps
4Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (77 mg) was dissolved in 5 ml of benzene at room temperature. N-bromosuccinimide (33 mg) and 5 mg of 2, 2′-azobis(isobutyronitrile) were added to the solution. The mixture was stirred for 10 min. Dichloromethane (10 ml) and 10 ml of semisaturated brine were added thereto, followed by separation. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to give 70 mg of 4-nitrobenzyl (1S,5R,6S)-2-(5-bromo-7-methylthioimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06677331B2 |
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| Source dataset | uspto-grants-2004_01 |
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| ORD ID | ord-e3902f8ca3d14111a669b49a5e55e6ca |
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| Source note | uspto-grants-2004_01 |
|---|