Hydrazine → HCID 19424602, compound

HRID 743501Notes

Reaction equation

HRID 743501 reaction equation
[CH2:1]1[N:8]([CH2:9][CH2:10][NH+:11]([CH2:22][C:23]([O-:25])=[O:24])[CH2:12][CH2:13][N:14]2[CH2:21][C:19](=[O:20])[O:18][C:16](=[O:17])[CH2:15]2)[CH2:7][C:5](=[O:6])[O:4][C:2]1=[O:3].C1CN2C(=NCCC2)C1.[NH2:35][NH2:36]>CS(C)=O>[C:16]([CH2:15][N:14]1[CH2:21][C:19](=[O:20])[NH:36][NH:35][C:5](=[O:6])[CH2:7][N:8]([CH2:1][C:2]([OH:4])=[O:3])[CH2:9][CH2:10][N:11]([CH2:22][C:23]([OH:25])=[O:24])[CH2:12][CH2:13]1)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 1676040123911-26-4

Product 1

HCID 19424602HCID 19424602, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

A 500 mL three-neck flask is charged with 150 mL of dry DMSO and flushed with nitrogen. Two syringes are charged separately with solutions of diethylenetriaminepentaacetic acid dianhydride (2.82 g, 7.89 mmol) and DBN (2.94 g, 2.92 mL, 23.67 mmol) in 122 mL of DMSO and anhydrous hydrazine (0.25 g, 0.25 mL, 7.89 mmol) in 125 mL DMSO. The two solutions are added simultaneously at the rate of 40 mL/hour to the flask at ambient temperature, employing a syringe pump. After the completion of addition the reaction mixture is stirred for 48 hours, concentrated under vacuum to 10 mL, and water (10 mL) is added. The solution at pH 10.5 is applied to AGIX-8 (100-200 mesh, acetate form) resin and the column is eluted with 1N acetic acid. The product is obtained by removal of acetic acid, followed by lyophilization.

Workup

  1. customflushed with nitrogen
  2. additionThe two solutions are added simultaneously at the rate of 40 mL/hour to the flask at ambient temperature
  3. additionAfter the completion of addition the reaction mixture
  4. concentrationconcentrated under vacuum to 10 mL, and water (10 mL)
  5. additionis added
  6. washthe column is eluted with 1N acetic acid
  7. customThe product is obtained by removal of acetic acid

Sources & evidence

ORD record
ord-7f3e6872f2b543e7932801a9b2c5a547
Source dataset
uspto-grants-1996_09
Patent number
US05556968

Reaction notes

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