Acetic Anhydride → HCID 18633397, compound

HRID 232370Notes

Reaction equation

HRID 232370 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([N:11]([CH2:13][C@H:14]1[O:18][C@@H:17]([N:19]2[CH:26]=[C:25]([CH2:27][CH3:28])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:16][C@@H:15]1[OH:29])[CH3:12])=[O:10].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([O:29][C@@H:15]1[C@@H:14]([CH2:13][N:11]([CH3:12])[C:9](=[O:10])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[O:18][C@@H:17]([N:19]2[CH:26]=[C:25]([CH2:27][CH3:28])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:16]1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18633406HCID 18633406, compound

Product 1

HCID 18633397HCID 18633397, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.05 g of 5'-[2-(2-bromophenyl)-N-methylacetamido]-2',5'-dideoxy-5-ethyluridine was dissolved in 2 ml of dry pyridine and the solution was treated with 0.12 ml of acetic anhydride. The mixture was stirred at room temperature for 5 hours and then evaporated. The residue was re-evaporated with toluene to give a solid which was triturated with diethyl ether and then removed by filtration. There was obtained 0.03 g of 3'-O-acetyl-5'-[2-(2-bromophenyl)-N-methylacet-amido]-2',5'-dideoxy-5-ethyluridine of melting point about 170° C.

Workup

  1. customevaporated
  2. customThe residue was re-evaporated with toluene
  3. customto give a solid which
  4. customwas triturated with diethyl ether
  5. customremoved by filtration

Sources & evidence

ORD record
ord-3ea2b025c52d41d690b547d9953b53f0
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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