Imidazole → t-Butyldimethylsilyloxyserine methyl ester

HRID 1734684Notes

Reaction equation

HRID 1734684 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CN(C=[O:27])C>CCOCC>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][O:27][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 22856314t-Butyldimethylsilyloxyserine methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

Serine methyl ester hydrochloride [HOCH2CH(NH2)CO2CH3. HCl] (18.7 g; 0.120 mol) and imidazole (30 g; 0.44 mol) are dissolved in DMF (100 ml) and cooled to 0° C. t-Butyldimethylsilyl chloride (19.5 g; 0.13 mol) is added and the reaction allowed to stir 15 hours at 25° C. The reaction is then diluted with ether (2 L), washed with water (4x 500 ml), dried (MgSO4) and concentrated to yield t-butyldimethylsilyloxyserine methyl ester as an oil which is used directly in Step B.

Workup

  1. additionis added
  2. washwashed with water (4x 500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e6de6bce13894bee8a8e60dfb2cbcae9
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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