Hydrazine hydrate (1:1) → HCID 54075093, compound

HRID 1769221Notes

Reaction equation

HRID 1769221 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][N:8]2[C:23](=[O:24])[C:22]([CH3:25])=[CH:21][N:10]([C@@H:11]3[O:17][C@H:14]([CH2:15][OH:16])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]3)[C:9]2=[O:26])C(=O)C2=CC=CC=C12.O.NN>CCO>[NH2:5][CH2:6][CH2:7][N:8]1[C:23](=[O:24])[C:22]([CH3:25])=[CH:21][N:10]([C@@H:11]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)[C:9]1=[O:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 465659HCID 465659, compound

Product 1

HCID 54075093HCID 54075093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 100 mg 3-PHT-E-AZT (Example 25) in 1 ml absolute EtOH was treated with 25 ul hydrazine hydrate, incubated overnight at room temperature and chromatographed by preparative TLC on silica gel-F 1000 um using the solvent system CHCl3 /MeOH/15M NH4OH (90+10+1). The UV positive band at Rf =0.25 was eluted with MeOH. Analytical TLC of the methanol extract in the same solvent system with silica gel-F 250 um showed the product to be homogeneous and ninhydrin positive. In this system a hydrazine reference migrated close to the origin as a UV negative, ninhydrin positive spot and reference phthalhydrazide remained at the origin as a UV positive, ninhydrin negative spot.

Workup

  1. customchromatographed by preparative TLC on silica gel-F 1000 um
  2. washThe UV positive band at Rf =0.25 was eluted with MeOH
  3. extractionAnalytical TLC of the methanol extract in the same solvent system with silica gel-F 250 um
  4. customIn this system a hydrazine reference migrated close to the origin as a UV negative, ninhydrin positive spot and reference phthalhydrazide

Sources & evidence

ORD record
ord-2d7877b8bc5a4fb2b8333877f9500e7a
Source dataset
uspto-grants-1995_01
Patent number
US05380825

Reaction notes

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