Succinic anhydride → HCID 86587256, compound

HRID 618465Notes

Reaction equation

[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1>>[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[C:20]([OH:25])(=[O:26])[CH2:21][CH2:22][C:23]([OH:6])=[O:24]

Participants

Reactant 2

HCID 7922Succinic anhydride

HCID 35370Zidovudine

Product 1

HCID 86587256HCID 86587256, compound

Procedure

AZT was reacted with succinic anhydride to form AZT-succinic acid. This was reacted by the DCC/HOSu method with a mixture of Gly-Tris-Mono, Di and Tripalmitate (GTPn) which was prepared by catalytic hydrogenation of Z-GTPn. Column chromatography on silica gel and preparative HPLC were used to isolate the final compounds:

Sources & evidence

ORD record: ord-972792e2d7104c66ac444fd08a7b39e8
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952499

Reaction notes

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