Imidazole → t-Butyldimethylsilyloxyserine methyl ester

HRID 863848Notes

Reaction equation

HRID 863848 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 (4×500 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 (4×500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6214c12aa284476c8675703628a13572
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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