Acat-IN-2 → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(2-hydroxy-ethylamino)-2,6-diisopropyl-phenyl ester

HRID 2289695Notes

Reaction equation

HRID 2289695 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([O:11][S:12](=[O:33])(=[O:32])[NH:13][C:14](=[O:31])[CH2:15][C:16]2[C:21]([CH:22]([CH3:24])[CH3:23])=[CH:20][C:19]([CH:25]([CH3:27])[CH3:26])=[CH:18][C:17]=2[CH:28]([CH3:30])[CH3:29])=[C:4]([CH:34]([CH3:36])[CH3:35])[CH:3]=1.[C:37](O)(=[O:39])[CH3:38].O>>[OH:39][CH2:37][CH2:38][NH:1][C:2]1[CH:3]=[C:4]([CH:34]([CH3:36])[CH3:35])[C:5]([O:11][S:12](=[O:33])(=[O:32])[NH:13][C:14](=[O:31])[CH2:15][C:16]2[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:18][C:19]([CH:25]([CH3:26])[CH3:27])=[CH:20][C:21]=2[CH:22]([CH3:23])[CH3:24])=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:7]=1

Participants

3

Reactant 2

HCID 10142595Acat-IN-2HCID 21899381Acetic acid--water (1/1)

Product 1

HCID 53706508[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(2-hydroxy-ethylamino)-2,6-diisopropyl-phenyl ester

Procedure

[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-amino-2,6-diisopropyl-phenyl ester (1.0 g, 1.9 mmol) was suspended in 50 mL of 1:1 glacial acetic acid/water and a stream of ethylene oxide was bubbled in for 15 minutes. The reaction mixture was sealed and allowed to stir overnight. The reaction mixture was concentrated in vacuo and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. Dried the organic layer over magnesium sulfate, filtered, and concentrated to give an oily solid. Chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.07 g of the title compound as a tan solid; mp 149-152° C.

Workup

  1. customa stream of ethylene oxide was bubbled in for 15 minutes
  2. customThe reaction mixture was sealed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompartitioned between saturated aqueous sodium bicarbonate and dichloromethane
  5. dry with materialDried the organic layer over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oily solid

Sources & evidence

ORD record
ord-f346fb760d2e45b1803b6d53a605c79f
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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