Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | m-Toluidine | HCID 7934 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 2-Bromopropionic acid, (S)- | HCID 642232 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 40989960 | HCID 40989960 | — |
Reaction Steps
To a solution of (S)-(−)-2-bromopropionic acid (0.25 mL, 2.77 mmol), m-toluidine (0.30 mL, 2.77 mmol) and 1-hydroxybenzotriazole hydrate (560 mg, 4.16 mmol) in tetrahydrofuran (25 mL) was added a 1M solution of 1,3-dicyclohexylcarbodiimide in dichloromethane (5.54 mL, 5.54 mmol). The mixture was stirred at about 0° C. for about 2 hours, then it was warmed to room temperature and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (2:1) as eluent to provide the desired product. MS (DCI-NH3): m/z 259, 261 (M+NH4)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07468371B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-b95a9e7c145546fe83ca3d53c0aae671 |
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| Source note | uspto-grants-2008_12 |
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