Dichloroacetic Acid → HCID 70399831, compound

HRID 1638978Notes

Reaction equation

HRID 1638978 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10]O)[O:8][C@@H:7]([N:12]2[CH:19]=[C:18]([CH2:20][CH3:21])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:6]1)(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.ClC(Cl)C(O)=O.[Cl:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([Cl:50])[C:45]=1[CH2:51][C:52](=[O:73])[CH:53]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CS(C)=O.N1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:9](/[CH:10]=[CH:53]/[C:52](=[O:73])[CH2:51][C:45]2[C:46]([Cl:50])=[CH:47][CH:48]=[CH:49][C:44]=2[Cl:43])[O:8][C@@H:7]([N:12]2[CH:19]=[C:18]([CH2:20][CH3:21])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6597Dichloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 18635822HCID 18635822, compoundHCID 19840120HCID 19840120, compound

Product 1

HCID 70399831HCID 70399831, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

A solution of 2.759 g of 3'-O-acetyl-2'-deoxy-5-ethyluridine, 5.75 g of dicyclohexylcarbodiimide and 0.375 ml of dichloroacetic acid in 24 ml of dimethyl sulphoxide was stirred at room temperature for 27 hours. 0.375 ml of pyridine and 4.286 g of [3-(2,6-dichlorophenyl)-2-oxopropylidene]triphenylphosphorane were added and the mixture was stirred for a further 23 hours. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in 100 ml of ethyl acetate and the solution was washed twice with 100 ml of water each time, dried over anhydrous sodium sulphate and evaporated. The resulting gum was subjected to flash chromatography on a column of silica gel using ethyl acetate/hexane (2:1) for the elution. There were obtained 3.84 g of (E)-3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2-oxopropylidene]-2',5'-dideoxy-5-ethyluridine in form of a white solid of melting point 165° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  4. washthe solution was washed twice with 100 ml of water each time
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. washfor the elution

Sources & evidence

ORD record
ord-f6634929673d44de815e142ef45bbea9
Source dataset
uspto-grants-1989_11
Patent number
US04882316

Reaction notes

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