Butyryl chloride → 3'-O-butyryl-5'-[2-(2,6-dichlorophenyl)acetamido]-2',5'-dideoxy-5-ethyluridine

HRID 1085518

Reaction equation

HRID 1085518 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:12][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])=[O:11].[C:30](Cl)(=[O:34])[CH2:31][CH2:32][CH3:33]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:30]([O:29][C@@H:15]1[C@@H:14]([CH2:13][NH:12][C:10](=[O:11])[CH2:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[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:34])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 8855Butyryl chlorideHCID 186334402-(2,6-Dichloro-phenyl)-N-[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-acetamide

Product 1

HCID 186334013'-O-butyryl-5'-[2-(2,6-dichlorophenyl)acetamido]-2',5'-dideoxy-5-ethyluridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 400 mg of 5'-[2-(2,6-dichlorophenyl)acetamido]2',5'-dideoxy-5-ethyluridine, 0.15 ml of butyryl chloride and 1 mg of 4-dimethylaminopyridine in 50 ml of pyridine was stored at room temperature overnight and then evaporated. The residue was subjected to flash chromatography on a column of silica geI using dichloromethane/methanol (24:1) for the elution, there being obtained 175 mg of 3'-O-butyryl-5'-[2-(2,6-dichlorophenyl)acetamido]-2',5'-dideoxy-5-ethyluridine in the form of a white solid of melting point 130°-132° C.

Workup

  1. customevaporated
  2. washfor the elution, there

Sources & evidence

ORD record
ord-e991ee60c9454c47b7cbde23ec678bd3
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Linked notes

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