tert-Butanol → HCID 86668203, compound
Reaction equation
P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:2]C1C=CC=CC=1.C([N:22]([CH2:25][CH3:26])[CH2:23]C)C.[CH3:27][C:28]1[O:32][N:31]=CC=1C(O)=O.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>C([O-])(O)=O.[Na+]>[CH3:27][C:28]1[O:32][N:31]=[CH:26][C:25]=1[NH:22][C:23](=[O:2])[O:40][C:36]([CH3:39])([CH3:38])[CH3:37]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Diphenyl phosphorazidate (1083 mg, 3.93 mmol) and triethylamine (0.55 ml, 3.93 mmol) was added to a stirred solution of 5-methylisoxazole-4-carboxylic acid (500 mg, 3.93 mmol) in tert-butanol (30 ml) at 50° C. After addition, the solution was heated at 90° C. for 6 hours. The reaction mixture was diluted with saturated NaHCO3 solution (50 ml) and then extracted with ethyl acetate (60 ml×5). The combined organic phases were dried over anhydrous MgSO4, and concentrated. The residue was purified by column chromatography column (silica gel, 40 g, eluent: dichloromethane/methanol=100:1, 1.3 L) to yield the title compound as a white solid. 161 mg,
Workup
- additionAfter addition
- extractionextracted with ethyl acetate (60 ml×5)
- dry with materialThe combined organic phases were dried over anhydrous MgSO4
- concentrationconcentrated
- customThe residue was purified by column chromatography column (silica gel, 40 g, eluent: dichloromethane/methanol=100:1, 1.3 L)
Sources & evidence
- ORD record
- ord-4d85b8435412436caffc0065743bb49f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
Loading…