(Bis(2-methoxyethyl)amino)sulfur trifluoride → (1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

HRID 1917344노트

반응식

HRID 1917344 반응식
[C:1]([O:5][C:6]([C@@:8]12[CH2:15][CH:14](O)[CH2:13][C@@H:12]1[C:11](=[O:17])[N:10]([C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)[F:36])CCOC>C(Cl)Cl>[C:1]([O:5][C:6]([C@:8]12[CH2:15][CH:14]([F:36])[CH2:13][C@H:12]1[C:11](=[O:17])[N:10]([C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67491063(1S,5S)-7-Hydroxy-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

생성물 1

HCID 67491056(1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(1S,5S)-7-Hydroxy-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester (1.0 g, 2.89 mmol) was dissolved in methylene chloride (15 mL). Bis(2-methoxyethyl)aminosulfur trifluoride (BAST) (0.59 mL) was added under ice-cooling, and the mixture was stirred at the same temperature for one hour. The reaction solution was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and filtered. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1→4:1→1:1) to give 711 mg (71%) of the title compound as a colorless oil.

후처리

  1. temperaturecooling
  2. washThe reaction solution was washed with saturated sodium bicarbonate water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThen, the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1→4:1→1:1)

출처 및 근거

ORD 기록
ord-f04276c0ba33455088a1a1ad260ff00d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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