Ammonium Chloride → (1S,5R)-5-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

HRID 1917338ノート

反応式

HRID 1917338 の反応式
[C:1]([O:5][C:6]([C@@:8]1([CH2:23][CH2:24]COS(C2C=CC=CC=2)(=O)=O)[CH:12]([F:13])[C:11](=[O:14])[N:10]([C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][Si](C)(C)[N-][Si](C)(C)C.[K+].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]12[CH2:23][CH2:24][CH2:36][C@:12]1([F:13])[C:11](=[O:14])[N:10]([C@@H:15]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:16])[CH2:9]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86664648(3S)-3-(3-benzenesulfonyloxy-1-propyl)-4-Fluoro-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 67490944(1S,5R)-5-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

(3S)-3-(3-benzenesulfonyloxy-1-propyl)-4-Fluoro-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (10.9 g) was dissolved in tetrahydrofuran (350 mL), and the atmosphere was replaced with argon. Then, potassium hexamethyldisilazide (0.5 M solution in toluene) (86.5 mL) was added dropwise at −15° C., and the mixture was stirred at 0° C. for 1.5 hours. After cooling to −10° C., saturated aqueous ammonium chloride (100 mL) was added dropwise, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was extracted with a 10% citric acid solution and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. Thereafter, the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=9:1→7:1) to give 4.36 g of the title compound as a pale yellow solid.

後処理

  1. temperatureAfter cooling to −10° C.
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. extractionThe reaction solution was extracted with a 10% citric acid solution and ethyl acetate
  4. washThen, the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThereafter, the solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-619d2c53a0d54559b45140b212c39ec6
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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