Imidazole → N-[(Phenylmethoxy)carbonyl]-O-[(1,1-dimethylethyl)dimethlsilyl]-L-homoserine

HRID 52806

Reaction equation

HRID 52806 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:9]1([CH2:15][O:16][C:17]([NH:19][C@H:20]([C:24]([OH:26])=[O:25])[CH2:21][CH2:22][OH:23])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CN=C1.CO>CN(C)C=O>[C:9]1([CH2:15][O:16][C:17]([NH:19][C@H:20]([C:24]([OH:26])=[O:25])[CH2:21][CH2:22][O:23][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6])=[O:18])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 489187Cbz-L-Homoserine

Product 1

HCID 54368725N-[(Phenylmethoxy)carbonyl]-O-[(1,1-dimethylethyl)dimethlsilyl]-L-homoserine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[(1,1-Dimethylethyl)dimethylsilyl]chloride (37.5 g., 249 mmol.) was added to a solution of N-[(phenylmethoxy)carbonyl]-L-homoserine [prepared as described in Example 6(a), 41.56 mmol.] in dimethylformamide (125 ml.), followed by imidazole (33.95 g., 498 mmol.). The resulting light yellow solution was stirred at room temperature for 22 hours. Methanol (500 ml.) was added, the reaction mixture was stirred for an additional 6 hours, and then the methanol and most of the dimethylformamide were removed in vacuo. The remaining residue was taken up into ethyl acetate (800 ml.), washed with 10% citric acid (2×300 ml.), and the combined aqueous phase was extracted with ethyl acetate (300 ml.). The combined ethyl acetate phase was washed with water and brine, dried (sodium sulfate), concentrated, and the residue was evaporated with hexane to form a white powder. This powder was dried in vacuo to give 12.942 g. of title product.

Workup

  1. stirringthe reaction mixture was stirred for an additional 6 hours
  2. customthe methanol and most of the dimethylformamide were removed in vacuo
  3. washwashed with 10% citric acid (2×300 ml.)
  4. extractionthe combined aqueous phase was extracted with ethyl acetate (300 ml.)
  5. washThe combined ethyl acetate phase was washed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customthe residue was evaporated with hexane
  9. customto form a white powder
  10. customThis powder was dried in vacuo
  11. customto give 12.942 g

Sources & evidence

ORD record
ord-0fc771a71c974358a5f5b9a640a2e38f
Source dataset
uspto-grants-1997_04
Patent number
US05616775

Linked notes

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