Water → methyl 7-(2-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 1388046노트

반응식

HRID 1388046 반응식
[NH:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]3[O:15][CH2:14][CH2:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[CH:20]=2)=[N:4][N:3]=[N:2]1.[H-].[Na+].[CH3:23]I.O>CN(C=O)C>[CH3:23][N:3]1[NH:2][N:1]=[C:5]([C:6]2[CH:7]=[CH:8][C:9]3[O:15][CH2:14][CH2:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[CH:20]=2)[NH:4]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178496911HCID 178496911, 화합물

생성물 1

HCID 18472406methyl 7-(2-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In DMF (6 ml) was dissolved methyl 7-(1H-tetrazol-5-yl)-2.3-dihydro-1-benzoxepine-4-carboxylate (400 mg, 1. 47 mmol), and to the mixture was added at 0° C. sodium hydride (60%, 90 mg, 2.3 mmol). The mixture was stirred at the same temperature for 15 minutes, and to the mixture was added at 0° C. methyl iodide (0.28 ml, 4.4 mmol). While the temperature of the mixture was warmed from 0° C. to room temperature, the mixture was stirred for 3 hours. To the mixture was added at 0° C. water (30 ml), and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 40 g, ethyl acetate/hexane=1/8→1/2), and the first eluted desired fraction was concentrated under reduced pressure to give methyl 7-(2-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate (334 mg, 1.17 mmol, 79%). The second eluted desired fraction was concentrated under reduced pressure to give methyl 7-(1-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate (76 mg, 0.27 mmol, 18%).

후처리

  1. temperatureWhile the temperature of the mixture was warmed from 0° C. to room temperature
  2. stirringthe mixture was stirred for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with column chromatography (silica gel 40 g, ethyl acetate/hexane=1/8→1/2)
  7. washthe first eluted desired fraction
  8. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3ca5de8243934f5384436aeccc506433
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268354B1

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