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

HRID 2371892노트

반응식

HRID 2371892 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.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]

참가 물질

7

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 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
-30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c4823de5812949748b880edb56bb44d5
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05096899

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