Ammonia → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 575879노트

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HRID 575879 반응식
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([O:20]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:28].O.CCCCCC.C(OCC)(=O)C>ClCCl>[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH2:28])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 57389439HCID 57389439, 화합물

생성물 1

HCID 57389435(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

60 mg of (2S,5R)-2,5-dioxopyrrolidin-1-yl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate was dissolved in dehydrated dichloromethane (0.8 mL), followed by cooling to 0° C. 0.12 mL of concentrated aqueous ammonia was added to the reaction solution, followed by stirring at room temperature for 1 hour. Subsequently, water (10 mL) was added and the organic layer was fractionated, followed by sequential washing with water and saturated brine and drying over anhydrous magnesium sulfate. The residue resulting from concentration of the solvent under reduced pressure was applied to silica gel column chromatography (hexane/ethyl acetate=1/3), and subsequently crystallized with chloroform/hexane=1:3 to afford 30.4 mg of the title compound as a colorless crystalline powder.

후처리

  1. washby sequential washing with water and saturated brine
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. customThe residue resulting from concentration of the solvent under reduced pressure
  4. customsubsequently crystallized with chloroform/hexane=1:3

출처 및 근거

ORD 기록
ord-276c0e03f9354e858a792a589f0e475d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035062B2

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