Succinic anhydride → HCID 86587256, compound

HRID 618466Notes

Reaction equation

HRID 618466 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>CN(C1C=CN=CC=1)C.CN(C=O)C>[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

5

Reactant 2

HCID 7922Succinic anhydrideHCID 35370Zidovudine

Product 1

HCID 86587256HCID 86587256, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

AZT (1.068 g, 4 mmol), succinic anhydride (0.440 g, 4.4 mmol) and DMAP (0.015 g) were weighed into a 25 ml flask fitted with a condenser. DMF (10 ml) was added and the mixture stirred for 5 min and immersed into an oil bath preheated to 90° C. for 1.5 h until HPLC assay indicated completion of reaction. DMF was evaporated under vacuum (<40° C.) and the residue used directly for the subsequent reaction. The residue can be purified by chromatography on silica gel and the product isolated in >87% yield and 97% purity if required.

Workup

  1. customfitted with a condenser
  2. customimmersed into an oil bath
  3. waitpreheated to 90° C. for 1.5 h until HPLC assay
  4. customcompletion of reaction
  5. customDMF was evaporated under vacuum (<40° C.)
  6. customthe residue used directly for the subsequent reaction
  7. customThe residue can be purified by chromatography on silica gel
  8. customthe product isolated in >87% yield and 97% purity

Sources & evidence

ORD record
ord-51ecd8dda1694a2bae0139ff881b399c
Source dataset
uspto-grants-1999_09
Patent number
US05952499

Reaction notes

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