Acetic Anhydride → HCID 18633398, compound

HRID 232385Notes

Reaction equation

HRID 232385 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][C:17]([NH:19][CH2:20][C@H:21]2[O:25][C@@H:24]([N:26]3[CH:33]=[C:32]([CH2:34][CH3:35])[C:30](=[O:31])[NH:29][C:27]3=[O:28])[CH2:23][C@@H:22]2[OH:36])=[O:18])=[C:11]([CH3:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38](OC(=O)C)(=[O:40])[CH3:39]>N1C=CC=CC=1>[C:38]([O:36][C@@H:22]1[C@@H:21]([CH2:20][NH:19][C:17](=[O:18])[CH2:16][C:12]2[C:11]([CH3:37])=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][C:13]=2[CH3:15])[O:25][C@@H:24]([N:26]2[CH:33]=[C:32]([CH2:34][CH3:35])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:23]1)(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53686061HCID 53686061, compound

Product 1

HCID 18633398HCID 18633398, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.25 g of 5'-[2-(4-benzyloxy-2,6-dimethylphenyl)acetamido]-2',5'-dideoxy-5-ethyluridine was stirred as a slurry in 5 ml of dry pyridine with 0.4 ml of acetic anhydride for 72 hours. The resulting solution was evaporated in vacuo and the residue was re-evaporated three times with toluene. After trituration with diethyl ether and filtration there was obtained 0.22 g of crude product of melting point 188°-191° C. Recrystallization from a mixture of 4 ml of methylene chloride and 4 ml of petroleum ether gave 0.20 g of pure 3'-O-acetyl-5'-[2-(4-benzyloxy-2,6-dimethylphenyl)acetamido]-2',5'-dideoxy-5-ethyluridine of melting point 194°-196° C. (dec).

Workup

  1. customThe resulting solution was evaporated in vacuo
  2. customthe residue was re-evaporated three times with toluene
  3. filtrationAfter trituration with diethyl ether and filtration there
  4. customwas obtained 0.22 g of crude product of melting point 188°-191° C
  5. customRecrystallization
  6. additionfrom a mixture of 4 ml of methylene chloride and 4 ml of petroleum ether

Sources & evidence

ORD record
ord-aec3ca33deca4f6eb40aec2b4b58dcd6
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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