Hydrazine hydrate (1:1) → HCID 53942049, compound

HRID 728761Notes

Reaction equation

HRID 728761 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:24](=[O:25])[C:23]([CH3:26])=[CH:22][N:11]([C@@H:12]3[O:18][C@H:15]([CH2:16][OH:17])[C@@H:14]([N:19]=[N+:20]=[N-:21])[CH2:13]3)[C:10]2=[O:27])C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:24](=[O:25])[C:23]([CH3:26])=[CH:22][N:11]([C@@H:12]2[O:18][C@H:15]([CH2:16][OH:17])[C@@H:14]([N:19]=[N+:20]=[N-:21])[CH2:13]2)[C:10]1=[O:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54362158HCID 54362158, compound

Product 1

HCID 53942049HCID 53942049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of approximately 0.5 mmole 3-PHT-P AZT (Example 26) in methanol was treated with 50 ul hydrazine hydrate and incubated overnight at room temperature. The resulting suspension was filtered through a 0.45 um PTFE membrane and the filtrate chromatographed by preparative TLC on silica gel-F 2000 um using the solvent system CHCl3 /MeOH/15M NH4OH (85+15+1). The major band (Rf =0.27; UV positive; ninhydrin positive)was well separated from 3-PHT-P-AZT (Rf =0.78; UV positive; ninhydrin negative) and from hydrazine (Rf =0.0; UV negative; ninhydrin postive). The product was eluted with MeOH. It was found to be immunologically active in an AZT assay by FPIA, was homogeneous on analytical TLC and its UV spectrum resembled that of a 3-alkylated AZT derivative.

Workup

  1. filtrationThe resulting suspension was filtered through a 0.45 um PTFE membrane
  2. customthe filtrate chromatographed by preparative TLC on silica gel-F 2000 um
  3. customninhydrin positive)was well separated from 3-PHT-P-AZT (Rf =0.78; UV positive; ninhydrin negative) and from hydrazine (Rf =0.0; UV negative; ninhydrin postive)
  4. washThe product was eluted with MeOH

Sources & evidence

ORD record
ord-613b26fd79514b429e3b78b6843aaa3b
Source dataset
uspto-grants-1991_09
Patent number
US05051361

Reaction notes

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