Hydrochloric Acid → HCID 86640942, compound

HRID 424334Notes

Reaction equation

HRID 424334 reaction equation
[C:1]([O:6][CH:7]1[CH:14]2[CH:10]3[CH:11]([CH:16]([C:17](Cl)=[O:18])[CH:8]1[CH2:9]3)[C:12](=[O:15])[O:13]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].[F:20][C:21]([F:28])([S:24]([O-:27])(=[O:26])=[O:25])[CH2:22][OH:23].[C:29]1([S+:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[F:20][C:21]([F:28])([S:24]([O-:27])(=[O:26])=[O:25])[CH2:22][O:23][C:17]([CH:16]1[CH:11]2[CH:10]3[CH:14]([CH:7]([O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH:8]1[CH2:9]3)[O:13][C:12]2=[O:15])=[O:18].[C:42]1([S+:35]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 86632756Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonateHCID 866409437-Chlorocarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-6-yl Methacrylate

Product 1

HCID 86640942HCID 86640942, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2.8 g (10 mmol) of the 2-methacryloyloxy-5-oxo-4-oxa-tricyclo[4.2.1.03,7]-non-9-ylcarbonyl chloride were added 4.2 g (10 mmol) of triphenylsulfonium 1,1-difluoro-2-hydroxy-ethanesulfonate in Synthesis Example 1-13 and 20 g of methylene chloride. To the mixture under ice cooling, a solution containing 1.0 g (10 mmol) of triethylamine and 0.25 g (2 mmol) of N,N-dimethylaminopyridine in 5 g of methylene chloride was added at a temperature below 5° C., and the resulting mixture was stirred for 2 hours at room temperature. Thereafter, 11 g of 5% dilute hydrochloric acid was added to the reaction mixture. The organic layer was taken out and washed with water, from which methylene chloride was distilled off in vacuum. 30 g of methyl isobutyl ketone was added to the residue, from which the residual water was distilled off in vacuum together with methyl isobutyl ketone. The resulting residue was purified by silica gel chromatography, obtaining the target compound, triphenylsulfonium 1,1-difluoro-2-(9-methacryloyloxy-4-oxo-5-oxatricyclo[4.2.1.03,7]-non-2-ylcarbonyloxy)-ethane-1-sulfonate. Colorless solids, 4.0 g (yield 61%). The compound has the following structure.

Workup

  1. additionwas added at a temperature below 5° C.
  2. washwashed with water, from which methylene chloride
  3. distillationwas distilled off in vacuum
  4. addition30 g of methyl isobutyl ketone was added to the residue, from which the residual water
  5. distillationwas distilled off in vacuum together with methyl isobutyl ketone
  6. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c3357e168a25405f8b426011fcf626e8
Source dataset
uspto-grants-2012_01
Patent number
US08105748B2

Reaction notes

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