Thionyl Chloride → HCID 18633406, compound

HRID 232367Notes

Reaction equation

HRID 232367 reaction equation
[CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[N:7]([CH:17]=1)[C@@H:8]1[O:16][C@H:12]([CH2:13][NH:14][CH3:15])[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28](Cl)=[O:29].S(Cl)(Cl)=O>N1C=CC=CC=1.C1C=CC=CC=1.C(Cl)Cl.CO>[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28]([N:14]([CH2:13][C@H:12]1[O:16][C@@H:8]([N:7]2[CH:17]=[C:3]([CH2:1][CH3:2])[C:4](=[O:19])[NH:5][C:6]2=[O:18])[CH2:9][C@@H:10]1[OH:11])[CH3:15])=[O:29]

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 41383862-Bromophenylacetyl chlorideHCID 18633445HCID 18633445, compound

Product 1

HCID 18633406HCID 18633406, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 1049PyridineSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

0.72 g of 2',5'-dideoxy-5-ethyl-5'-methylaminouridine in 25 ml of dry pyridine was stirred at 0° C. and treated with a solution of (2-bromophenyl)acetyl chloride (prepared from 0.65 g of the acid by treatment with thionyl chloride in benzene under reflux) in 7 ml of benzene. The mixture was stirred at 0° C. for 0.5 hour and then stored at 4° C. overnight. The solvents were removed by evaporation and the residue was re-evaporated with toluene to give a gum which was subsequently triturated with diethyl ether to yield a solid. This solid was taken up in 5 ml of methylene chloride/methanol (9:1) and chromatographed on a column of silica gel using methylene chloride/methanol (9:1) for the elution. The fractions containing the product were combined and evaporated. The residue was re-evaporated with ethanol and recrystallized from methanol to give 0.18 g of 5'-[2-(2-bromophenyl)-N-methylacetamido]-2',5'-dideoxy-5-ethyluridine of melting point 182° -185° C.

Workup

  1. waitstored at 4° C. overnight
  2. customThe solvents were removed by evaporation
  3. customthe residue was re-evaporated with toluene
  4. customto give a gum which
  5. customwas subsequently triturated with diethyl ether
  6. customto yield a solid
  7. customchromatographed on a column of silica gel
  8. washfor the elution
  9. additionThe fractions containing the product
  10. customevaporated
  11. customThe residue was re-evaporated with ethanol
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a99ed81a5c7f45738b05baa990d3fa78
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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