Imidazole → (S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate
Reaction equation
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][C@@H:11]([OH:16])[CH2:12][C:13]([NH2:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:17])[CH2:10][C@@H:11]([O:16][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:12][C:13]([NH2:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
(S)-Benzyl-3-hydroxyglutaramate (100 g) was dissolved in dimethyl formamide. To this Imidazole (35 g) was added and the solution was cooled to 5° C. To this a solution of tert-butyldimethylsilylchloride (68.5 g) dissolved in dimethyl formamide (250 ml) was added under cooling. The mixture was warmed to 20-25° C. and stirred. The reaction mixture was cooled and quenched with water. To the reaction mixture ethyl acetate and water was added and stirred. The layers were separated and the organic phase was washed thrice with water. The organic phase was evaporated under reduced pressure to yield (S)-benzyl-3-(tert-butyl dimethylsilyloxy)glutaramate as oil.
Workup
- additionwas added
- temperatureunder cooling
- temperatureThe mixture was warmed to 20-25° C.
- temperatureThe reaction mixture was cooled
- customquenched with water
- additionTo the reaction mixture ethyl acetate and water was added
- stirringstirred
- customThe layers were separated
- washthe organic phase was washed thrice with water
- customThe organic phase was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-2c28ce0d3abe4c76b8897459480dc206
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273333B2
Reaction notes
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