Azobisisobutyronitrile → D-Glucosamine

HRID 2188041Notes

Reaction equation

HRID 2188041 reaction equation
C(N)(=O)C=C.C([NH:10][C@@H:11]1[C@@H:17]([OH:18])[C@H:16]([OH:19])[C@@H:15]([CH2:20][OH:21])[O:14][CH:12]1[OH:13])(=O)C=C.C(NN[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O)(=O)C=C.SCCNC(=O)C(NC(=O)C1C=CC(C(=O)C2C=CC=CC=2)=CC=1)CCCCNC(=O)C1C=CC(C(=O)C2C=CC=CC=2)=CC=1.CC(N=NC(C#N)(C)C)(C#N)C.CN(CCN(C)C)C>O>[OH:13][CH:12]1[O:14][C@H:15]([CH2:20][OH:21])[C@@H:16]([OH:19])[C@H:17]([OH:18])[C@H:11]1[NH2:10]

Participants

8

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 6579AcrylamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 14455563HCID 14455563, compoundHCID 18477245HCID 18477245, compoundHCID 86758276HCID 86758276, compound

Product 1

HCID 439213D-Glucosamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acrylamide (400mg, 5.6 mmole) was dissolved in 10 ml of dimethylsulfoxide(DMSO). To that solution was added 400 mg (1.48 mmole) of N-acryloylglucosamine (Compound VI). Additionally were added 34 mg of N-(2-mercaptoethyl)-2,6-bis(4-benzoylbenzamido)hexanamide, 200 mg of AIBN and 50 μl of TEMED. The solution was sparged with nitrogen, then placed in a 55° C. oven overnight. The resulting polymer solution was dialyzed against deionized water using SpectraPor 1 (Spectrum) dialysis membrane. After dialysis, the solution was lyophilized. The dried polymer obtained was 0.58 gm by weight. At 0.1 mg/ml in deionized water, the polymer had an absorbance at 265 nm of 0.202.

Workup

  1. customThe solution was sparged with nitrogen
  2. customplaced in a 55° C.
  3. customovernight
  4. customThe resulting polymer solution was dialyzed against deionized water using SpectraPor 1 (Spectrum) dialysis membrane
  5. customAfter dialysis
  6. customThe dried polymer obtained

Sources & evidence

ORD record
ord-200b9cd63cb444ac8016aff88c28bde3
Source dataset
uspto-grants-2002_06
Patent number
US06410643B1

Reaction notes

Loading…