Hydrochloric Acid → HCID 86640942, 화합물

HRID 424334노트

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HRID 424334 반응식
[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

참가 물질

6

반응물 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

생성물 1

HCID 86640942HCID 86640942, 화합물수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c3357e168a25405f8b426011fcf626e8
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08105748B2

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