Water → HCID 86585369, compound

HRID 433874

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](Cl)(=[O:25])[CH2:21][C:22](Cl)=[O:23].[OH2:27]>C(#N)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:6])[CH2:21][C:22]([OH:23])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

One gram of AZT was dissolved in 30 ml of anhydrous acetonitrile and added dropwise to a solution of 632 mg of malonyl chloride in 20 ml of acetonitrile at 0° C. The reaction mixture was stirred for 2 hours at 0° C. then at 8-10° C. for 4.5 hours. Thin layer chromatography was used to indicate that the reaction was complete. Water (4 ml) was added. Solvents were removed in vacuo and the residue purified by silica gel chromatography eluting with CHCl3:MeOH. Pure product was obtained in a 68% yield.

Workup

waitat 8-10° C. for 4.5 hours
customSolvents were removed in vacuo
customthe residue purified by silica gel chromatography
washeluting with CHCl3
customPure product was obtained in a 68% yield

Sources & evidence

ORD record: ord-7b4e75d009ce4e7f9b25fb3eb70d387c
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670341B1

Linked notes

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