Triethylamine → Zidovudine

HRID 1769223Notes

Reaction equation

HRID 1769223 reaction equation
NCCC[N:5]1[C:20](=[O:21])[C:19]([CH3:22])=[CH:18][N:7]([C@@H:8]2[O:14][C@H:11]([CH2:12][OH:13])[C@@H:10]([N:15]=[N+:16]=[N-:17])[CH2:9]2)[C:6]1=[O:23].CCN(CC)CC>CO>[CH3:22][C:19]1[C:20](=[O:21])[NH:5][C:6](=[O:23])[N:7]([C@@H:8]2[O:14][C@H:11]([CH2:12][OH:13])[C@@H:10]([N:15]=[N+:16]=[N-:17])[CH2:9]2)[CH:18]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 53942049HCID 53942049, compound

Product 1

HCID 35370Zidovudine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10 mg MTAF (Example 31), 10 mg of 3-AP-AZT (Example 28) and 2.5 ul Et3N in 250 ul MeOH was incubated 90 minutes at 56° C., then 24 hours at room temperature and chromatographed twice over RPF 250 um using the solvent system MeOH/H2O/HOAc (50+50+3). The product (Rf =0.25) was homogeneous on TLC and was found to provide a satisfactory tracer for quantitation of AZT by FPIA.

Workup

  1. custom24 hours at room temperature and chromatographed twice over RPF 250 um

Sources & evidence

ORD record
ord-dede9430bdd1443580c71402d0c14159
Source dataset
uspto-grants-1995_01
Patent number
US05380825

Reaction notes

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