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

HRID 2084894Notes

Reaction equation

HRID 2084894 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[C:17]([O-:19])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].N1C=CN=[CH:36]1>CN(C=O)C.CCOCC>[CH3:36][O:18][C:17](=[O:19])[CH:16]([C:20]1[CH:21]=[CH:22][C:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:24][CH:25]=1)[NH:15][S:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)(=[O:14])=[O:13]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86590202[{[4-(2-Butynyloxy)phenyl]sulfonyl}amino](4-hydroxyphenyl)acetate

Product 1

HCID 53702579[4-(Tert-butyl-dimethyl-silanyloxy) phenyl](4-but-2-ynyloxy-benzenesulfonylamino)-acetic acid methyl esterYield 82,451.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

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-1fb3494a86104476afc2234c6fe6d77f
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

Loading…