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

HRID 1031042노트

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HRID 1031042 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
-30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39555710e1bc46829693a0f4ad1f1377
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05108747

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