Acetic Anhydride → N-(5-t-butyl-3-isoxazolyl)isobutyramide
Reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:23])[C:12]([CH3:22])(SCC2CCCNC2)[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.C(OC(=O)C)(=O)C>>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:23])[CH:12]([CH3:13])[CH3:22])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
A solution of 175 mg (0.52 mmol) of N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(piperidin-3-ylmethylsulfanyl)-propionamide 0.18 mL (1.04 mmol) of N,N-diisopropylethylamine and acetic anhydride (1.5 mL) were heated for 0.5 h to 100° C. within a microwave (CEM discover). The solvent was removed under reduced pressure. The residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (5 mL). The organic phase was dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure to afford 183 mg of 241-acetyl-piperidin-3-ylmethylsulfanyl)-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide, which was used in the next step without further purification.
Workup
- customThe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in DCM (5 mL)
- washwashed with saturated aqueous NaHCO3 solution (5 mL)
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-32af91b7a1094d33aed4b94cd22533e5
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829034B2
Reaction notes
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