Imidazole → 2-Amino-4-(tert-butyldimethylsilanyloxy)butyric acid

HRID 8529

Reaction equation

HRID 8529 reaction equation
N1C=CN=C1.[NH2:6][C@H:7]([C:11]([OH:13])=[O:12])[CH2:8][CH2:9][OH:10].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>CN(C=O)C>[NH2:6][CH:7]([CH2:8][CH2:9][O:10][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 12647L-HomoserineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 220157142-Amino-4-(tert-butyldimethylsilanyloxy)butyric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (20.4 g, 300 mmol) is added to a solution of homoserine (11.9 g, 100 mmol) in DMF (100 mL) and the solution is stirred 15 minutes then cooled to 0° C. tert-Butyldimethylsilyl chloride (13.7 g, 91 mmol) added and the mixture is stirred for ten minutes at 0° C. the for 4 hours at room temperature. The reaction mixture is poured into water (3 L) and the resulting solid is collected by filtration. The isolated product is dried and used without further purification.

Workup

  1. additionadded
  2. stirringthe mixture is stirred for ten minutes at 0° C. the for 4 hours at room temperature
  3. filtrationthe resulting solid is collected by filtration
  4. customThe isolated product is dried
  5. customused without further purification

Sources & evidence

ORD record
ord-65bf027c2ce34a99952537c84cd0ebc0
Source dataset
uspto-grants-2006_08
Patent number
US07087759B2

Linked notes

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