Water → 3,4-Diethyl-2-azetidinone

HRID 335344노트

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HRID 335344 반응식
[CH2:1]([CH:3]1[CH:6]([CH2:7][CH3:8])[C:5](=[O:9])[N:4]1S(Cl)(=O)=O)[CH3:2].C1(S)C=CC=CC=1.N1C=CC=CC=1.O>CC(C)=O>[CH2:7]([CH:6]1[CH:3]([CH2:1][CH3:2])[NH:4][C:5]1=[O:9])[CH3:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 7969ThiophenolHCID 14190960(2RS,3RS)-2,3-Diethyl-4-oxoazetidine-1-sulfonyl Chloride

생성물 1

HCID 141909823,4-Diethyl-2-azetidinone

시약·촉매·용매 1

HCID 180Acetone용매2회

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온도
-30 °C

실험 절차

(2RS,3RS)-2,3-Diethyl-4-oxoazetidine-1-sulfonyl chloride (step 1) (3.2 g, 14.18 mmol) in acetone (7 ml) was treated with thiophenol (2.92 ml, 28.4 mmol) and cooled to −30° C. Pyridine (1.376 ml, 17.01 mmol) in acetone (2.55 ml) was added dropwise over 30 mins, maintaining the temperature around −30° C. After stirring for 30 minutes, water (10 ml) was added slowly and the mixture was filtered. The filtrate was extracted with diethyl ether (5×25 ml) and the combined organic layers were dried MgSO4, filtered and evaporated to dryness (colorless oil 2.3 g). Purification by chromatography on silica eluting with iso-hexane followed by diethyl ether afforded the title compound;

후처리

  1. temperaturemaintaining the temperature around −30° C
  2. filtrationthe mixture was filtered
  3. extractionThe filtrate was extracted with diethyl ether (5×25 ml)
  4. filtrationfiltered
  5. customevaporated to dryness (colorless oil 2.3 g)
  6. customPurification by chromatography on silica eluting with iso-hexane

출처 및 근거

ORD 기록
ord-ebd48e91b5974b179ab4cd9224afe72a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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