Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyanogen Bromide | HCID 10476 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 67515007 | HCID 67515007 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 49853813 | HCID 49853813 | 26% |
Reaction Steps
To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (0.2 g, 0.57 mmol) in DMF (5 mL) were added DIPEA (0.3 mL, 1.7 mmol) and cyanogen bromide (0.18 g, 1.1 mmol) at r.t. The reaction mixture was stirred at 100° C. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3) to provide the title compound (0.05 g, 26%) as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08906913B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-ca2cc7e977a54b739e1f4299374eaf0c |
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| Source note | uspto-grants-2014_12 |
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