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

HRID 870865
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인쇄 미리보기

반응식

HRID 870865 반응식
C(Cl)CCl.[CH2:5]([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]([OH:24])=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.O[NH:36][C:37](=[NH:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39]>CN(C=O)C>[CH2:5]([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[O:24][N:43]=[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acidHCID 178472862HCID 178472862, 화합물

생성물 1

HCID 86701408ethyl 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxylate수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

EDC (0.916 g, 4.78 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (1.2 g, 4.34 mmol) and HOBt (0.732 g, 4.78 mmol) in DMF (12 mL) at rt. The mixture was stirred at rt for 0.5 h, then ethyl 2-(hydroxyamino)-2-iminoacetate (0.689 g, 5.21 mmol) was added and the mixture was stirred for another 0.5 h at rt. The reaction mixture was then heated to 100° C. under microwave for 80 minutes. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography (0 to 5% MeOH/DCM) to afford ethyl 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazole-3-carboxylate (0.85 g, 53%). ESI-MS (EI+, m/z): 373.4.

후처리

  1. stirringthe mixture was stirred for another 0.5 h at rt
  2. temperatureThe reaction mixture was then heated to 100° C. under microwave for 80 minutes
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by silica gel column chromatography (0 to 5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-fb4c55da70a3459784c7b816c84459fd
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969570B2

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