Hydrochloric Acid → (3R,4S)-1-t-butyldimethylsilyl-3-ethyl-3-methylazetidin-2-one-4-carboxylic acid

HRID 484044ノート

反応式

HRID 484044 の反応式
[CH:1](NC(C)C)(C)[CH3:2].C([Li])CCC.[Si:13]([N:20]1[C@H:23]([C:24]([OH:26])=[O:25])[C@@H:22]([CH3:27])[C:21]1=[O:28])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(I)C.Cl>C1COCC1.CCCCCC.CCOCC>[Si:13]([N:20]1[C@H:23]([C:24]([OH:26])=[O:25])[C@:22]([CH2:1][CH3:2])([CH3:27])[C:21]1=[O:28])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 7912DiisopropylamineHCID 10014678(2S,3R)-1-(tert-butyldimethylsilyl)-3-methyl-4-oxoazetidine-2-carboxylic acidHCID 178418339Butyllithium

生成物 1

HCID 10061758(3R,4S)-1-t-butyldimethylsilyl-3-ethyl-3-methylazetidin-2-one-4-carboxylic acid

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

To a solution of 13 mL of diisopropylamine in 75 mL of THF at -20° C. was added 35 mL of 2.4M n-butyl lithium in hexane. After 15 minutes the solution was cooled to -70° C. and a solution of 10 gms of (3R,4S)-1-t-butyldimethylsilyl-3-methylazetidin-2-one-4-carboxylic acid in 50 mL of THF was added. The solution was warmed to -20° C. for 15 minutes and a solution of 6.7 mL of ethyl iodide in 10 mL of THF was added. After 30 minutes at -20° to 0° C. the reaction was diluted with ether and poured into a mixture of ice and 1N HCl. The layers were separated and the aqueous layer extracted with ether. The ether layers were each washed with brine, dried over sodium sulfate and evaporated. The residue was crystallized from a minimum amount of hexane to give 8.8 gms of (3R,4S)-1-t-butyldimethylsilyl-3-ethyl-3-methylazetidin-2-one-4-carboxylic acid.

後処理

  1. temperatureThe solution was warmed to -20° C. for 15 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ether
  4. washeach washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was crystallized from a minimum amount of hexane

出典と根拠

ORDレコード
ord-daa6f20f0ebd4ead99eaa07d8e743f4e
出典データセット
uspto-grants-1993_07
特許番号
US05229381

反応ノート

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