Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 68768788 | HCID 68768788 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68771244 | HCID 68771244 | 93.2% |
Reaction Steps
To a solution of 1-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}cyclopropane-carboxamide hydrochloride (0.50 g, 1.30 mmol) in DMF (5.0 mL) was added acetic anhydride (0.15 g, 1.43 mmol). The reaction mixture was cooled to 0° C., and DIEA (0.34 g, 2.6 mmol) was added slowly over 1 h. The reaction was allowed to stir at 0° C. After 1.5 h, the reaction mixture was diluted with H2O (20 mL) and washed with EtOAc (2×30 mL). The organic layers were combined and washed with H2O (2×20 mL), dried over MgSO4, filtered, and concentrated to give the title compound (0.473 g, 93%). LC/MS: Rt=1.78 min, ES+391 (Formic Acid method).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07838673B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-f761a2401d6a484f989b00ca8507ce8b |
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| Source note | uspto-grants-2010_11 |
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