Imidazole → [4-(Tert-butyl-dimethyl-silanyloxy) phenyl](4-but-2-ynyloxy-benzenesulfonylamino)-acetic acid methyl ester

HRID 1976432Notes

Reaction equation

HRID 1976432 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15](C)[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=2)[C:17](NO)=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].N1C=CN=C1.CN([CH:46]=[O:47])C>CCOCC>[CH3:46][O:47][C:17](=[O:18])[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:23][CH:22]=1)[NH:15][S:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:11][CH:10]=1)(=[O:13])=[O:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 99538082-[{[4-(2-Butynyloxy)Phenyl]Sulfonyl}(Methyl)Amino]-N-Hydroxy-2-(4-Methoxyphenyl)Acetamide

Product 1

HCID 53702579[4-(Tert-butyl-dimethyl-silanyloxy) phenyl](4-but-2-ynyloxy-benzenesulfonylamino)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6.62 g (0.017 mmol) of [}[4-(2-butynyloxy)phenyl]sulfonyl}amino](4-hydroxyphenyl)acetate from Example 178 in 50 mL of DMF was added 3.08 g (0.020 mmol) of tert-butyldimethylsilyl chloride followed by 2.89 g (0.043 mmol) of imidazole. The reaction was stirred at room temperature for 5 h and then diluted with ether. The resulting mixture was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to give 7.06 g of [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(4-but-2-ynyloxy-benzenesulfonylamino)-acetic acid methyl ester as a white solid. Electrospray Mass Spec 504.4 (M+H)+

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-604ee6f4b151416ba0d47669ca73e089
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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