Imidazole → (S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate

HRID 921502Notes

Reaction equation

HRID 921502 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]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 89601064(S)-Benzyl-3-hydroxyglutaramate

Product 1

HCID 125499654(S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(S)-Benzyl-3-hydroxyglutaramate (49.5 g) was dissolved in anhydrous dimethylformamide (50 ml) and added to a 500 ml flask containing solid imidazole (17.1 g). To this a solution of tert-butyldimethylsilyl chloride (34 g) in dimethylformamide (120 ml) was added and reaction flask was cooled in an ice-bath. The reaction was quenched by addition of water-saturated ethyl acetate. The mixture was stirred at ambient temperature. To this water was added and the biphasic mixture was stirred for 1 hour. The mixture was then washed with water. The organic phases were mixed and washed with water to remove traces of dimethylformamide. The organic phase was evaporated under reduced pressure to yield (S)-benzyl-3-(tert-butyl dimethylsilyloxy)glutaramate.

Workup

  1. additionadded to a 500 ml flask
  2. customreaction flask
  3. temperaturewas cooled in an ice-bath
  4. customThe reaction was quenched by addition of water-saturated ethyl acetate
  5. additionTo this water was added
  6. stirringthe biphasic mixture was stirred for 1 hour
  7. washThe mixture was then washed with water
  8. additionThe organic phases were mixed
  9. washwashed with water
  10. customto remove traces of dimethylformamide
  11. customThe organic phase was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ef076b2aecd4c04aa2d50babc6c418a
Source dataset
uspto-grants-2016_03
Patent number
US09273333B2

Reaction notes

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