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

HRID 1072629Notes

Reaction equation

HRID 1072629 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-2f25c78d9e7843e4abf6c5f04ea0568a
Source dataset
uspto-grants-2005_06
Patent number
US06911447B2

Reaction notes

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