Sodium Bicarbonate → HCID 19350839, compound

HRID 1636294Notes

Reaction equation

HRID 1636294 reaction equation
[F:1][C:2]1[C:3](=[O:24])[NH:4][C:5](=[O:23])[N:6]([CH:8]2[CH2:13][S:12][CH:11]([CH2:14][O:15]CC3C=CC=CC=3)[CH2:10][O:9]2)[CH:7]=1.CO.C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:3](=[O:24])[NH:4][C:5](=[O:23])[N:6]([CH:8]2[CH2:13][S:12][CH:11]([CH2:14][OH:15])[CH2:10][O:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 19350829HCID 19350829, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 19350839HCID 19350839, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-Fluoro-1-(5-benzyloxymethyl-1,4-oxathian-2-yl)uracil (0.46 g) was dissolved in methylene chloride (50 ml), and the solution cooled to -78° C. To the solution, t-boron trichloride (13.1 ml) was added dropwise, and the mixture stirred at the same temperature for 4 hours. After adding a mixture of methanol-methylene chloride (1/1, 14 ml) and then sodium bicarbonate thereto, the resultant mixture was stirred at room temperature. Upon filtering the mixture to remove solid materials, the filtrate was concentrated, and the residue was purified on a silica gel column chromatography (eluent: chloroform/methanol=15/1) to obtain the desired product (0.11 g) as pale yellow solid.

Workup

  1. additionAfter adding
  2. filtrationUpon filtering the mixture
  3. customto remove solid materials
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified on a silica gel column chromatography (eluent: chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-d60f6c1e3ada407da3c347f550e2ca3a
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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