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Aziridine → HCID 11290689, 화합물

HRID 1058506
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HRID 1058506 반응식
Cl[C:2]1[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:16]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8].[NH:23]1[CH2:25][CH2:24]1>C(Cl)Cl>[N:23]1([C:2]2[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:16]=2)[C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8])[CH2:25][CH2:24]1
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참가 물질

4

반응물 2

HCID 9033AziridineHCID 11404780HCID 11404780, 화합물

생성물 1

HCID 11290689HCID 11290689, 화합물수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred solution of the above amide (315 mg, 0.95 mmol) in CH2Cl2 (35 mL) was treated with aziridine (197 μL, 3.81 mmol) at room temperature for 8 h. The mixture was partitioned between more CH2Cl2 and water, and the organic layer was dried and concentrated under reduced pressure. The residue was dissolved in EtOAc and filtered through a short column of silica gel to give 8 (269 mg, 84%): mp (CH2Cl2/iPr2O) 137° C.; 1H NMR [(CD3)2SO] δ8.86 (t, J=5.6 Hz, 1 H, NH), 8.66 (s, 1H, H-3), 7.40 (s, 1H, H-6), 3.63 (s, 3H, Me), 3.51-3.43 (m, 2H, NHCH2), 2.61 (t, J=6 8 Hz, 2H, CH2CO), 2 48 (s, 4H, aziridine-H). Anal. Calcd for C13H14N4O7: C, 46.15;H, 4 17; N, 16 57. Found: C, 45.89,H, 3.89; N, 16.45%.

후처리

  1. customThe mixture was partitioned between more CH2Cl2 and water
  2. customthe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. filtrationfiltered through a short column of silica gel

출처 및 근거

ORD 기록
ord-6a6ff077b85a4b75840ba69f52bb6406
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06517836B1

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