Acetyl chloride → 3-Acetyl-3'-azido-5'-O-(3-chlorobenzoyl)-3'-deoxythymidine

HRID 973795Notes

Reaction equation

HRID 973795 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][C:11](=[O:19])[C:12]2[CH:17]=C[C:15](Cl)=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:20]2[CH:28]=[C:26]([CH3:27])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:5]1)=[N+:2]=[N-:3].[C:29](Cl)(=[O:31])[CH3:30].[CH:33]([Cl:36])(Cl)Cl.CO>C1C=CC=CC=1.[Ag]C#N>[C:29]([N:23]1[C:24](=[O:25])[C:26]([CH3:27])=[CH:28][N:20]([C@@H:6]2[O:7][C@H:8]([CH2:9][O:10][C:11](=[O:19])[C:12]3[CH:13]=[CH:14][CH:15]=[C:33]([Cl:36])[CH:17]=3)[C@@H:4]([N:1]=[N+:2]=[N-:3])[CH2:5]2)[C:21]1=[O:22])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 186478033'-azido-5'-O-(4-chlorobenzoyl)-3'-deoxythymidineHCID 21584188Chloroform methanol

Product 1

HCID 186477993-Acetyl-3'-azido-5'-O-(3-chlorobenzoyl)-3'-deoxythymidineYield 64%

Reagents, catalysts & solvents 2

HCID 178509332CID 101611454CatalystHCID 241BenzeneSolvent

Procedure

To a mixture of 3'-azido-5'-O-(4-chlorobenzoyl)-3'-deoxythymidine (0.3 g, 0.74 mMol) and silver cyanide (0.4 g, 3.0 mMol) in 20 mL of benzene, excess acetyl chloride (2.6 g, 33 mMol) was added in several portions. The mixture was stirred at room temperature until the starting material disappeared (4 hours) as established by TLC CHCl3 /MeOH 20:1 (v/v). The reaction was filtered and the filtrate evaporated under reduced pressure to dryness. The resulting oily residue was chromatographed on silica gel eluted with chloroform/hexane 1:1 (v/v) followed by chloroform to give 0.21 g (64%) of the desired product as an oil.

Workup

  1. additionwas added in several portions
  2. custom(4 hours)
  3. filtrationThe reaction was filtered
  4. customthe filtrate evaporated under reduced pressure to dryness
  5. customThe resulting oily residue was chromatographed on silica gel
  6. washeluted with chloroform/hexane 1:1 (v/v)

Sources & evidence

ORD record
ord-bec77de7f2084b37aec0e6dc988af035
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Reaction notes

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