3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-(1-hydroxyisopropyl)-5-phenylisoxazole → 3-(2-Aminoethoxy)-4-isopropenyl-5-phenylisoxazole hydrochloride

HRID 612901Notes

Reaction equation

HRID 612901 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17](O)([CH3:19])[CH3:18])=[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:14][N:13]=1)=O)(C)(C)C.[ClH:27].O1CCOCC1>>[ClH:27].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17]([CH3:19])=[CH2:18])=[C:15]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:14][N:13]=1

Participants

3

Reactant 2

HCID 195965303-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-(1-hydroxyisopropyl)-5-phenylisoxazoleHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 195965933-(2-Aminoethoxy)-4-isopropenyl-5-phenylisoxazole hydrochlorideYield 83%

Conditions

Temperature
100 °C

Procedure

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-(1-hydroxyisopropyl)-5-phenylisoxazole (0.13 g) was dissolved in a 4N hydrochloric acid/1,4-dioxane solution (10 ml), and the solution was stirred at 100° C. for one hour. After the reaction, the reaction mixture was left to be cooled, followed by evaporation of the solvent under reduced pressure. The residue was washed with ethyl acetate to obtain the title compound (0.10 g, 83%) as colorless crystals.

Workup

  1. customAfter the reaction
  2. waitthe reaction mixture was left
  3. temperatureto be cooled
  4. customfollowed by evaporation of the solvent under reduced pressure
  5. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-f493ffc7cc574ba689329d75364963ae
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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