Hydroxylamine → 3-[(4-but-2-ynoxyphenyl)sulfonylamino]-N-hydroxypropanamide

HRID 2268286Notes

Reaction equation

HRID 2268286 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=O)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH:21][N:22]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.NO>CN(C)C=O.O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH2:17][C:18]([NH:22][OH:21])=[O:20])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15550575HCID 15550575, compound

Product 1

HCID 99267793-[(4-but-2-ynoxyphenyl)sulfonylamino]-N-hydroxypropanamideYield 35.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To N-{[4-(2-butynyloxy)phenyl]sulfonyl}-beta-alanine (0.80 g, 2.69 mmol) in dimethylformamide (5 mL) was added 1-hydroxybenzotriazole (0.436 g, 3.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.67 g, 3.5 mmol). After one hour 50% hydroxylamine in water (1.3 mL) was added. The reaction mixture was stirred overnight and concentrated in vacuo. Ethyl acetate was added and the organic phase washed with water (2×) and brine then dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave a white solid that was triturated with ethyl acetate to give 3-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-N-hydroxypropanamide (0.30 g) as a white solid,. mp 118-128° C. Electrospray Mass Spec 313.3 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEthyl acetate was added
  3. washthe organic phase washed with water (2×) and brine
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration in vacuo
  6. customgave a white solid
  7. customthat was triturated with ethyl acetate

Sources & evidence

ORD record
ord-7a840b8234864381b85cb9b49432053c
Source dataset
uspto-grants-2001_12
Patent number
US06326516B1

Reaction notes

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