Triethylamine → 2-(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-ethyl-1,3,4-oxadiazole

HRID 512616노트

반응식

HRID 512616 반응식
[Si:1]([O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][NH2:17])=[O:15])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[C:21](=N)(OCC)[CH2:22][CH3:23].CCN(CC)CC>CCO>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]2[O:15][C:21]([CH2:22][CH3:23])=[N:17][N:16]=2)=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 107079144-(Tert-butyldimethylsilyloxy)methylbenzhydrazideHCID 13000588Ethyl propanecarboximidate hydrochloride

생성물 1

HCID 584319792-(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-ethyl-1,3,4-oxadiazole수율 44%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)benzohydrazide (6.0 g, 21.4 mmol; reported in Tanaka, A. et al. J. Med. Chem. 1998, 41, 2390) and ethyl propionimidate hydrochloride (3.5 g, 25.7 mmol; preparation reported in WO2007/73299 A1) in EtOH (120 mL) was added Et3N (2.59 g, 25.7 mmol). The mixture was stirred at room temperature for 1 hr then concentrated in vacuo. The residue was partitioned into EtOAc and H2O and the organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (EtOAc-hexanes) gave 2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-ethyl-1,3,4-oxadiazole as a brown oil (3.0 g, 44% yield).

후처리

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned into EtOAc and H2O
  3. washthe organics were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-121278935be84851a21e3336c2f87766
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102643B2

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