Water → tert-Butyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate

HRID 1775320노트

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HRID 1775320 반응식
[OH:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[NH:4].[C:18](OC(=O)C)(=O)[CH3:19].O>N1C=CC=CC=1>[CH3:18][C:19]1[O:1][N:2]=[C:3]([N:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]2)[N:4]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

생성물 1

HCID 86686046tert-Butyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate수율 91.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
80 °C

실험 절차

To a solution of tert-butyl 4-(N-hydroxycarbamimidoyl)piperazine-1-carboxylate (771 mg, 3.16 mmol) in pyridine (8 mL) was added acetic anhydride (320 L, 3.42 mmol) and the reaction was heated to 80° C. for 3 h. The mixture was cooled to room temperature, poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure to yield 774 mg of a yellow solid. After purification by flash chromatography (silica, gradient of 0.5 to 3% methanol in dichloromethane) 509 mg of an off-white solid were obtained (1.897 mmol, 60%). MS (ESI) m/z=291.1 [M+Na]+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c4381c964faf4a398db4a678fee17190
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260441B2

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