Tetrahydrofuran → p-Nitrobenzyl (4-tert-butylthio-2-oxo-1-azetidinyl)acetate

HRID 1031042ノート

反応式

HRID 1031042 の反応式
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].[C:11]([S:15]N1CCC1=O)([CH3:14])([CH3:13])[CH3:12].Br[CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24].[O:36]1C[CH2:39][CH2:38][CH2:37]1>CN(C)C=O>[C:11]([S:15][CH:39]1[N:5]([CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:37](=[O:36])[CH2:38]1)([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 70153214-Nitrobenzyl bromoacetateHCID 19905241Tert-butylthioazetidin-2-one

生成物 1

HCID 14460289p-Nitrobenzyl (4-tert-butylthio-2-oxo-1-azetidinyl)acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-30 °C

実験手順

14.4 ml of 1 N solution of lithium bis-trimethylsilylamide in tetrahydrofuran (THF) are added dropwise with stirring at -70° C. to a solution of 1.91 g (12 mmol) of tert-butylthioazetidin-2-one in 6 ml of dry N,N-dimethylformamide (DMF) and then a solution of 4.93 g (18 mmol) of p-nitrobenzyl bromoacetate in 6 ml of DMF is added dropwise to the mixture and the mixture is stirred at -30° C. for a further 30 minutes. Dilution of the reaction mixture with 100 ml of toluene, washing with three portions of 50 ml each of water, drying the organic phase over magnesium sulphate and evaporating the solvent in vacuo yields 4.3 g of solid crude product, which is chromatographed on 120 g of silica gel using toluene/ethyl acetate (4:1). The purified product (2.6 g) is recrystallized from 100 ml of dry isopropanol.

後処理

  1. washDilution of the reaction mixture with 100 ml of toluene, washing with three portions of 50 ml each of water
  2. dry with materialdrying the organic phase over magnesium sulphate
  3. customevaporating the solvent in vacuo

出典と根拠

ORDレコード
ord-39555710e1bc46829693a0f4ad1f1377
出典データセット
uspto-grants-1992_04
特許番号
US05108747

反応ノート

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