Hydroxylamine → HCID 22644959, compound

HRID 2084900Notes

Reaction equation

HRID 2084900 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH:17]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:23][CH:22]=2)[C:18](O)=[O:19])[CH3:16])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH:37][N:38]1C2C=CC=CC=2N=N1.NO>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH3:16])[CH:17]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:33])[O:34][CH2:35][CH3:36])=[CH:25][CH:26]=2)[C:18]([NH:38][OH:37])=[O:19])(=[O:14])=[O:13])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 757711-HydroxybenzotriazoleHCID 69802538HCID 69802538, compound

Product 1

HCID 22644959HCID 22644959, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To [{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino}(4-{3-[(ethoxycarbonyl)amino]propoxy]phenyl)acetic acid (0.35 g, 0.67 mmol) and 1-(3-dimethyl aminopropyl) 3-ethyl carbodiimide (0.2 g, 1.01 mmol) in DMF (8 ml), 1-hydroxybenzotriazole (0.13 g, 0.95 mmol) was added and the reaction was stirred at room temperature for 2 h. Hydroxylamine (0.23 ml of 50% in water, 3.71 mmol) was added and the reaction was stirred overnight. After evaporating the solvent, the residue was extracted with ethyl acetate and water, the organic layer was washed with saturated NaHCO3, water and brine, dried over Na2SO4, and concentrated. The residue was purified with preparative TLC plates (eluting with ethyl acetate:methanol (85:15) to provide 0.1 g of ethyl 3-{4-[1-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-2-(hydroxyamino)-2-oxoethyl]phenoxy}propylcarbamate as a yellow solid. mp 60-62° C. Electrospray Mass Spec 532 (M+H)+.

Workup

  1. stirringthe reaction was stirred overnight
  2. customAfter evaporating the solvent
  3. extractionthe residue was extracted with ethyl acetate and water
  4. washthe organic layer was washed with saturated NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified with preparative TLC plates (
  8. washeluting with ethyl acetate:methanol (85:15)

Sources & evidence

ORD record
ord-409d9f7165114862b59a8b0a14852745
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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