Imidazole → HCID 14040059, compound
Reaction equation
N1C=CN=C1.[OH:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20].CCOC(C)=O.CCCCCC>ClCCl>[C:13]([O:12][C:11](=[O:17])[NH:10][CH2:9][CH2:8][CH2:7][O:6][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])([CH3:14])([CH3:16])[CH3:15]Participants
Procedure
11.6 g (1.3 eq) imidazole were added to a solution of 23 g (1 eq) tert-butyl 3-hydroxypropyl-carbamate in 230 ml dichloromethane. The reaction solution was stirred for 10 min at room temperature and then cooled to 0° C. 21.79 g (1.1 eq) TBDMSCl were added to this solution at 0° C. and on completion of the addition the mixture was stirred for 1 h at room temperature. The reaction course was monitored by thin-layer chromatography (30% EtOAc/hexane). Once the conversion was complete, the reaction mixture was filtered over celite and the filtrate mixed with 200 ml water and extracted with dichloromethane. The combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, 32 g (84%) of product were obtained in the form of an oil.
Workup
- temperaturecooled to 0° C
- stirringwas stirred for 1 h at room temperature
- filtrationthe reaction mixture was filtered over celite
- additionthe filtrate mixed with 200 ml water
- extractionextracted with dichloromethane
- dry with materialThe combined organic phases were dried over Na2SO4
- customremoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-45ffde803fe944e2b53c4c72169b5ad0
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206156B2
Reaction notes
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