Citric Acid → (2S,3R)-1-t-butyldimethylsilyl-3-benzyl-4-oxo-2-azetidinecarboxylic acid

HRID 2413701ノート

反応式

HRID 2413701 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[Si:13]([N:20]1[C:23](=[O:24])[CH2:22][C@H:21]1[C:25]([OH:27])=[O:26])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCOCC.CCCCCC>[Si:13]([N:20]1[C:23](=[O:24])[C@H:22]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:21]1[C:25]([OH:27])=[O:26])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

参加物

9

反応物 5

HCID 311Citric AcidHCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 10489602(2S)-1-[tert-Butyl(dimethyl)silyl]-4-oxoazetidine-2-carboxylic acidHCID 178418339Butyllithium

生成物 1

HCID 13824878(2S,3R)-1-t-butyldimethylsilyl-3-benzyl-4-oxo-2-azetidinecarboxylic acid収率 67%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

In 6 ml of THF was dissolved 836.3 mg of diisopropylamine and the solution was cooled to 0° C. in a nitrogen atmosphere. To the solution was gradually added 5.2 ml of a n-hexane solution containing 530 mg of n-butyl lithium at 0° C. The mixture was stirred for 10 minutes at the same temperature. Then, a solution of 920 mg of (S)-1-t-butyldimethylsilyl-4-oxo-2-azetidinecarboxylic acid (1) in 8 ml of dry THF was added to the mixture at 0° C. followed by stirring at room temperature for 30 minutes. The solution was cooled to 0° C. and 820.8 mg of benzyl bromide was added to the solution. The mixture was then stirred at room temperature for 30 minutes. The solution was again cooled to 0° C. and a 10% citric acid solution was added thereto to render acidic. Ether was added to the mixture to separate from the aqueous phase. After the ethereal phase was dried, the solvent was removed by distillation to obtain 858 mg of (2S,3R)-1-t-butyldimethylsilyl-3-benzyl-4-oxo-2-azetidinecarboxylic acid (2) showing a melting point of 99°~102° C. as colorless crystals.

後処理

  1. stirringby stirring at room temperature for 30 minutes
  2. temperatureThe solution was cooled to 0° C.
  3. stirringThe mixture was then stirred at room temperature for 30 minutes
  4. temperatureThe solution was again cooled to 0° C.
  5. customto separate from the aqueous phase
  6. customAfter the ethereal phase was dried
  7. customthe solvent was removed by distillation

出典と根拠

ORDレコード
ord-2531d4a5e89a47f89597347d0e796641
出典データセット
uspto-grants-1988_01
特許番号
US04719207

反応ノート

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