Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 69337972 | HCID 69337972 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69338013 | HCID 69338013 | 99.4% |
Reaction Steps
(2R)-Acetylamino-2-methyl-4-(thiophen-2-yl)butyl acetate (1.81 g, 6.70 mmol) obtained in Example 47(b) was dissolved in dimethylformamide (20 ml), and N-bromosuccinimide (1.27 g, 7.11 mmol) was added thereto in an ice bath followed by stirring under a nitrogen atmosphere for 10 minutes in an ice bath and then overnight at room temperature. The reaction solution was poured into water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:1-1:2) to afford the title compound (2.32 g, 99% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06723745B2 |
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| Source dataset | uspto-grants-2004_04 |
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| ORD ID | ord-912fb6102291476681693df3004c1c84 |
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| Source note | uspto-grants-2004_04 |
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