Imidazole → (Dimethoxyphosphinyl)[[(1,1-dimethylethyl)dimethylsilyl]oxy]acetic acid (4-nitrophenyl)methyl ester

HRID 54783

Reaction equation

HRID 54783 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12](=[O:21])[CH:13]([P:15]([O:19][CH3:20])([O:17][CH3:18])=[O:16])[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].N1C=CN=C1>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12](=[O:21])[CH:13]([P:15]([O:19][CH3:20])([O:17][CH3:18])=[O:16])[O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10064522Acetic acid, (dimethoxyphosphinyl)hydroxy-, (4-nitrophenyl)methyl ester

Product 1

HCID 9932571(Dimethoxyphosphinyl)[[(1,1-dimethylethyl)dimethylsilyl]oxy]acetic acid (4-nitrophenyl)methyl ester

Procedure

To a mixture of 3.48 g of product from Example 97 and 12 ml of dimethylformide is added 1.86 of t-butyldimethylsilyl chloride and 1.86 g of imidazole. After stirring the reaction at room temperature for 2 hours, the mixture is diluted with 50% ethyl acetate/diethyl ester, washed 5 times water, once with saturated solid bicarbonate and once with saturated solid chloride. The organic layer is dried, filtered and concentrated in vacuo to give 3.90 g of the desired silylated product.

Workup

  1. customthe reaction at room temperature for 2 hours
  2. washwashed 5 times water
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 3.90 g of the desired silylated product

Sources & evidence

ORD record
ord-176add45f66046e7b8a21502c35de5fd
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Linked notes

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