Acetonitrile → Salicylhydroxamic Acid

HRID 2227871Notes

Reaction equation

HRID 2227871 reaction equation
C(#N)C.[C:4](Cl)(=[O:8])[C:5](Cl)=O.C(N(CC)CC)C.[C:17]([NH2:25])(=[O:24])[CH2:18][CH2:19][CH2:20][C:21](N)=O.C([O-])(=[O:28])C.[Na+]>ClCCl>[OH:8][C:4]1[CH:5]=[CH:21][CH:20]=[CH:19][C:18]=1[C:17]([NH:25][OH:28])=[O:24]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 230227PentanediamideHCID 517045Sodium Acetate

Product 1

HCID 66644Salicylhydroxamic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ten milliliters of unmodified M280 or M450 magnetic beads (Dynal) were gradually dehydrated into acetonitrile, and converted to aldehyde modified beads using oxalyl chloride activated N,N-dimethylsulfoxide and triethylamine in dichloromethane at −78° C. The resulting aldehyde bearing beads were gradually rehydrated and suspended in 5 mL of 0.1 M sodium acetate pH 5.5. The aldehyde groups were coupled N′-[(4-(N-hydroxycarbamoyl)-3-hydroxy-phenyl)methyl]-N-(2-{N-[2-(4-{N-[(N-hydroxycarbamoyl)-3-hydroxyphenyl)methyl]carbamoyl}-butanoylamino)ethyl]-4-(N-aminocarbamoyl)butanoylamino}ethyl)pentane-1,5-diamide (21Y-SHA-hydrazide) by adding 25 milligrams dissolved in 200 uL N,N-dimethylsulfoxide, and rotating coupling reaction over night at room temperature. The beads were then washed extensively with water and stored in 5 mL of 10% ethanol.

Workup

  1. customat −78° C
  2. additionby adding 25 milligrams
  3. customcoupling reaction over night at room temperature
  4. washThe beads were then washed extensively with water

Sources & evidence

ORD record
ord-92d6b750268c4f8fa9ed2d01c5d05fb7
Source dataset
uspto-grants-2002_07
Patent number
US06414122B1

Reaction notes

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