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

HRID 2371892ノート

反応式

HRID 2371892 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.C1(C)C=CC=CC=1>[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

7

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 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-30 °C

実験手順

14.4 ml of a 1N solution of lithium bistrimethylsilylamide in tetrahydrofuran (THF) are added dropwise to a stirred solution of 1.91 g (12 mmol) of tert-butylthioazetidin-2-one in 6 ml of dry N,N-dimethylformamide (DMF) at -70° C., and a solution of 4.93 g (18 mmol) of p-nitrobenzyl bromoacetate in 6 ml of DMF is subsequently added dropwise to the mixture, and the mixture is then stirred for a further 30 minutes at -30° C. The reaction mixture is diluted with 100 ml of toluene and washed with three 50 ml portions of water, the organic phase is dried over magnesium sulphate, and the solvent is evaporated in vacuo to give 4.3 g of a solid crude product, which is chromatographed over 120 g silica gel using toluene:ethyl acetate (4:1). The purified product (2.6 g) is recrystallized from 100 ml of dry isopropanol. Yield 2.09 g of melting point 82.5°-84° C. IR spectrum in methylene chloride: 2955, 1770, 1755, 1610, 1530, 1390, 1375, 1365, 1345, 1180, 1110, 945, 915, 855, 845 cm-1.

後処理

  1. washwashed with three 50 ml portions of water
  2. dry with materialthe organic phase is dried over magnesium sulphate
  3. customthe solvent is evaporated in vacuo

出典と根拠

ORDレコード
ord-c4823de5812949748b880edb56bb44d5
出典データセット
uspto-grants-1992_03
特許番号
US05096899

反応ノート

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