Imidazole → HCID 67506454, compound
Reaction equation
C([O:9][C@H:10]([CH3:31])[C@H:11]1[O:15][C@@H:14]([N:16]2[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[C@H:13]([O:25][CH2:26][CH2:27][O:28][CH3:29])[C@@H:12]1[OH:30])(=O)C1C=CC=CC=1.N1C=CN=C1.[Si:37](Cl)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38]>CN(C=O)C.CCOC(C)=O.N>[CH3:29][O:28][CH2:27][CH2:26][O:25][C@@H:13]1[C@H:12]([O:30][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C@@H:11]([C@@H:10]([CH3:31])[OH:9])[O:15][C@H:14]1[N:16]1[CH:23]=[C:22]([CH3:24])[C:20](=[O:21])[NH:19][C:17]1=[O:18]Participants
Procedure
A mixture of Compound 10 (1.33 g, 3.06 mmol) and imidazole (2.09, 30.70 mmol) was dissolved in anhydrous DMF (11.4 mL). To this solution tert-butyldimethylsilyl chloride (2.31 g, 15.33 mmol) was added with stirring at room temperature for 16 h under an atmosphere of argon. The reaction mixture was diluted with EtOAc (75 mL) and washed with saturated aqueous NaHCO3 (2×60 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue obtained was dissolved in methanolic ammonia (20 mL, 7 M) and stirred for 24 h at 55° C. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography and eluted with 50% EtOAc in hexanes to yield Compound 11 (1.21 g, 89%). ES MS m/z 455.2 [M+H]+.
Workup
- washwashed with saturated aqueous NaHCO3 (2×60 mL) and brine (50 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue obtained
- stirringstirred for 24 h at 55° C
- customThe solvent was removed under reduced pressure
- customthe residue was purified by silica gel column chromatography
- washeluted with 50% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-34395f2a72914f0690cab0638b9fd398
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987435B2
Reaction notes
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