Acetic Anhydride → (1-Acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

HRID 2201690노트

반응식

HRID 2201690 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:23])[O:17][CH2:18][CH:19]1[CH2:22][NH:21][CH2:20]1)([O-:3])=[O:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:23])[O:17][CH2:18][CH:19]1[CH2:20][N:21]([C:24](=[O:26])[CH3:25])[CH2:22]1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 71007325Azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

생성물 1

HCID 71007323(1-Acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.35 g, 1.05 mmol, 1 eq.) in dichloromethane (10 mL) was added TEA (0.22 mL, 1.57 mmol, 1.5 eq.) and acetic anhydride (0.11 mL, 1.15 mmol, 1.1 eq.) at 0° C. The reaction was warmed to room temperature and stirred for 1 h. The reaction was diluted with dichloromethane. The organic layer was washed with water and brine. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 4% MeOH/CH2Cl2) to obtain (1-acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.31 g, 79% yield).

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography (silica gel, 4% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-de2f979d8fdc4a5f878261bd5d3c4cde
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365498B2

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