HCID 53968692, compound → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl ester

HRID 2289685Notes

Reaction equation

HRID 2289685 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]([O:16][S:17](=[O:38])(=[O:37])[NH:18][C:19](=[O:36])[CH2:20][C:21]2[C:26]([CH:27]([CH3:29])[CH3:28])=[CH:25][C:24]([CH:30]([CH3:32])[CH3:31])=[CH:23][C:22]=2[CH:33]([CH3:35])[CH3:34])=[C:9]([CH:39]([CH3:41])[CH3:40])[CH:8]=1)(C)(C)C>C(#N)C>[OH:6][C:7]1[CH:8]=[C:9]([CH:39]([CH3:41])[CH3:40])[C:10]([O:16][S:17](=[O:38])(=[O:37])[NH:18][C:19](=[O:36])[CH2:20][C:21]2[C:22]([CH:33]([CH3:34])[CH3:35])=[CH:23][C:24]([CH:30]([CH3:31])[CH3:32])=[CH:25][C:26]=2[CH:27]([CH3:29])[CH3:28])=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=1

Participants

3

Reactant 1

HCID 53968692HCID 53968692, compound

Product 1

HCID 10142635[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl esterYield 90.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 15 mL concentrated HF in 150 mL acetonitrile was added dropwise to a solution of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(tert-butyl-dimethyl-silanyloxy)-2,6-diisopropyl-phenyl ester (9.71 g, 15.4 mmol) in 400 mL acetonitrile at room temperature under a nitrogen atmosphere. Stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between water and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give an oily solid. Trituration with hexanes gave 7.24 g of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl ester as a white solid; mp 182-183° C.

Workup

  1. concentrationA solution of 15 mL concentrated HF in 150 mL acetonitrile
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily solid

Sources & evidence

ORD record
ord-73bad4f621a34a42aa125a6923d52264
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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