Sodium hydride → (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine

HRID 1464721노트

반응식

HRID 1464721 반응식
[H-].[Na+].[C:3]([SH:7])(=[S:6])[CH2:4][CH3:5].[CH2:8]([O:11][C:12]([N:14]1[CH2:18][C@H:17](OS(C)(=O)=O)[CH2:16][C@H:15]1[CH2:24][O:25][CH2:26][CH2:27][F:28])=[O:13])[CH:9]=[CH2:10]>O1CCCC1>[CH2:8]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([S:6][C:3](=[S:7])[CH2:4][CH3:5])[CH2:16][C@H:15]1[CH2:24][O:25][CH2:26][CH2:27][F:28])=[O:13])[CH:9]=[CH2:10]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10176109Propanedithioic AcidHCID 57165653(2S,4R)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methylsulfonyloxypyrrolidine

생성물 1

HCID 57310918(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of sodium hydride (60% in oil, 2.0 g) in anhydrous tetrahydrofuran (50 ml) was added propanedithioic acid (5.0 g) with ice-cooling. A solution of (2S,4R)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methylsulfonyloxypyrrolidine (16.25 g) in anhydrous tetrahydrofuran (50 ml) was added dropwise to the mixture and the mixture was heated at 60°-70° C. for 4 hours. The solution was poured into ice-water (100 ml) and extracted with diethyl ether. The organic layer was washed with 1N aqueous sodium hydroxide solution (50 ml) and brine, dried, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel [n-hexane-ethyl acetate (10:1, V/V)] to afford (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine (9.47 g).

후처리

  1. temperaturecooling
  2. temperaturethe mixture was heated at 60°-70° C. for 4 hours
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with 1N aqueous sodium hydroxide solution (50 ml) and brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel [n-hexane-ethyl acetate (10:1, V/V)]

출처 및 근거

ORD 기록
ord-7b7619e10011423fa6aec898a94e952e
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306816

반응 노트

불러오는 중…