Hydroxylamine → 2-({[4-(2,3-Butadienyloxy)phenyl]sulfonyl}amino)-N-hydroxy-3-methylbutanamide

HRID 1180542Notes

Reaction equation

HRID 1180542 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C@H:16]([C:20]([OH:22])=O)[CH:17]([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]=[CH2:4].[OH:23][N:24]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.NO>CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([CH:17]([CH3:19])[CH3:18])[C:20]([NH:24][OH:23])=[O:22])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]=[CH2:4]

Participants

7

Reactant 5

HCID 787HydroxylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86588656N-{[4-(2,3-Butadienyloxy)phenyl]sulfonyl}valine

Product 1

HCID 99025192-({[4-(2,3-Butadienyloxy)phenyl]sulfonyl}amino)-N-hydroxy-3-methylbutanamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of product from Example 12 (210 mg, 0.65 mmol) in dimethylformamide (6 ml) was added 1-hydroxybenzotriazol (105 mg, 0.78 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodimide hydrochloride (173 mg, 0.90 mmol), and N-methylmorpholine (0.106 mmol, 0.97 mmol) and the resulting mixture was stirred for 1 hour at room temperature. A 50% aqueous solution of hydroxylamine (0.119 ml, 1.94 mmol) was added and the mixture was stirred for 15 hours at room temperature. The reaction mixture was concentrated in vacuo, diluted with water, and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, saturated sodium bicarbonate, saturated sodium chloride and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave 100 mg (45%) of the product.

Workup

  1. stirringthe mixture was stirred for 15 hours at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with 1N hydrochloric acid, water, saturated sodium bicarbonate, saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-fbae94c06af64103a638c98674e48f28
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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