Methanol → HCID 67716928, compound

HRID 37399Notes

Reaction equation

HRID 37399 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[C:21]([CH3:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:24])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:27](OC)[N:28]([CH3:30])[CH3:29].CO>CN(C)C=O>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[C:21]([CH3:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:24])[C:11]1=[CH:27][N:28]([CH3:30])[CH3:29])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 78373Dimethylformamide dimethyl acetalHCID 67717591HCID 67717591, compound

Product 1

HCID 67716928HCID 67716928, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-5-methyl-2'-oxo-uridine (3.854 g, 10.9 mmol) from Step 3 was dissolved in 50 mL of dry dimethylformamide (DMF) and 1.74 mL (1.56 g, 13.1 mmol) of N,N-dimethylformamide dimethylacetal was added. The reaction mixture was heated in an oil bath at 50° C. for 40 min. The solvent was evaporated in vacuo and the residue purified on a silica gel column, the product eluting with 5% methanol in methylene chloride to give 2.512 g (56.3% yield) of the title compound, [α]D23 =-84.2° (C, 1.44, MeOH). DCI MS M/Z: (M+H)+ 410.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified on a silica gel column
  3. washthe product eluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-8b89ea9a18534cdc9f67e8204450b341
Source dataset
uspto-grants-1995_05
Patent number
US05420276

Reaction notes

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