Potassium Carbonate → HCID 53900167, compound

HRID 612799Notes

Reaction equation

HRID 612799 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:32]=[C:31]([C:33]#[C:34][Si](C)(C)C)[C:19]([NH:20][C:21]([O:23][CH2:24][C:25]([CH3:30])([CH3:29])[CH2:26][O:27][CH3:28])=[O:22])=[N:18][C:16]1=[O:17])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[C:33]([C:31]1[C:19]([NH:20][C:21]([O:23][CH2:24][C:25]([CH3:29])([CH3:30])[CH2:26][O:27][CH3:28])=[O:22])=[N:18][C:16](=[O:17])[N:15]([CH:32]=1)[C@@H:6]1[O:7][C@H:8]([CH3:14])[C@@H:9]([OH:10])[C@H:5]1[OH:4])#[CH:34]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53782845HCID 53782845, compound

Product 1

HCID 53900167HCID 53900167, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2',3'-di-O-acetyl-5'-deoxy-N4 -[(3-methoxy-2,2- dimethylpropoxy)carbonyl]-5-[2-(trimethylsilyl)ethynyl]-cytidine (100 mg, 0.18 mmol) was dissolved in methanol (4 ml), followed by addition of K2CO3 (38 mg,0.27 mmol). After stirring for 30 min at room temperature, the reaction mixture was evaporated under reduced pressure. Purification of the residue by preparative thin layer chlomatography on silica gel (using dichloromethane:methanol=20:1 as a developing solvent) gave 5'-deoxy-5- ethynyl-N4 -[(3-methoxy-2,2-dimethylpropoxy)carbonyl]cytidine (43 mg, 60%).

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customPurification of the residue by preparative thin layer chlomatography on silica gel (

Sources & evidence

ORD record
ord-4312fed29dac4f70885016e760c48566
Source dataset
uspto-grants-1999_12
Patent number
US06005098

Reaction notes

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