(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 1917344ノート

反応式

HRID 1917344 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-f04276c0ba33455088a1a1ad260ff00d
出典データセット
uspto-grants-2013_12
特許番号
US08618094B2

反応ノート

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