Ethyl chloroformate → 3,5-bis(benzyloxy)-N-[5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2-yl]benzamide

HRID 133702ノート

反応式

HRID 133702 の反応式
Cl[C:2](OCC)=[O:3].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:29][OH:30])=[NH:28])=[CH:23][N:22]=1)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH2:35]([O:34][C:32]1[CH:31]=[C:17]([CH:16]=[C:15]([O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[NH:28][C:2](=[O:3])[O:30][N:29]=2)=[CH:23][N:22]=1)=[O:19])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

4

反応物 2

HCID 10928Ethyl chloroformateHCID 178513344N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

生成物 1

HCID 1356089023,5-bis(benzyloxy)-N-[5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2-yl]benzamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Ethyl chloroformate (32 μL, 0.33 mmol) was added to a solution of 3,5-bis(benzyloxy)-N-{5-[(hydroxyamino)(imino)methyl]pyridin-2-yl}benzamide (140 mg, 0.30 mmol) in pyridine (5 mL). This solution was heated at reflux overnight. The mixture was cooled and concentrated under reduced pressure. DCM and methanol were used to dissolve the remaining material and the solution was washed with water. The organic solution was concentrated under reduced pressure and the residue was purified on silica by MPLC (eluting firstly with 5% methanol/DCM then 10% methanol/DCM). The title compound was obtained as a colourless solid (103 mg, 70%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 6.87 (1H, s); 7.28-7.46 (12H, m); 8.21 (1H, dd); 8.38 (1H, d); 8.79 (1H, s); 11.14 (1H, br s); m/z (LCMS; ESI+) 495 (MH+).

後処理

  1. temperatureThis solution was heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionto dissolve the remaining material
  6. washthe solution was washed with water
  7. concentrationThe organic solution was concentrated under reduced pressure
  8. customthe residue was purified on silica by MPLC (
  9. washeluting firstly with 5% methanol/DCM

出典と根拠

ORDレコード
ord-647193508d0e44c3b97c398bd6546ebc
出典データセット
uspto-grants-2008_06
特許番号
US07390908B2

反応ノート

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