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Ammonia → 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxamide

HRID 870867
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인쇄 미리보기

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HRID 870867 반응식
[NH3:1].CO.[CH2:4]([O:11][N:12]1[C:18](=[O:19])[N:17]2[CH2:20][C@H:13]1[CH2:14][CH2:15][C@H:16]2[C:21]1[O:25][N:24]=[C:23]([C:26]([O:28]CC)=O)[N:22]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)(C)C>[CH2:4]([O:11][N:12]1[C:18](=[O:19])[N:17]2[CH2:20][C@H:13]1[CH2:14][CH2:15][C@H:16]2[C:21]1[O:25][N:24]=[C:23]([C:26]([NH2:1])=[O:28])[N:22]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
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참가 물질

5

반응물 3

HCID 222AmmoniaHCID 887MethanolHCID 86701408ethyl 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxylate

생성물 1

HCID 867014125-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxamide수율 40%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
40 °C

실험 절차

Ammonia in MeOH solution (2.3 mL, 16.11 mmol) was added to a solution of ethyl 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxylate (600 mg, 1.61 mmol) in isopropanol (8 mL) and the reaction mixture was heated at 40° C. for 1 h. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography (0 to 10% MeOH/DCM) to afford 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxamide (220 mg, 40%). ESI-MS (EI+, m/z): 344.3.

후처리

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by silica gel column chromatography (0 to 10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-0a31237ef2324bafb07eddb1108a602f
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969570B2

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