Triethylamine → 4-(3,3-Diethyl-4-oxo-1-(phenylmethylaminocarbonyl)-2-(R, S)-azetidinyl)oxy-nitrobenzene

HRID 484194노트

반응식

HRID 484194 반응식
C(N(CC)CC)C.[CH2:8]([N:15]=[C:16]=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:18]([C:20]1([CH2:35][CH3:36])[C:23](=[O:24])[NH:22][CH:21]1[O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)[CH3:19].C(OCC)(=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:35]([C:20]1([CH2:18][CH3:19])[C:23](=[O:24])[N:22]([C:16]([NH:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:17])[CH:21]1[O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)[CH3:36]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 76639Benzyl isocyanateHCID 197510524-(3,3-Diethyl-4-oxo-2-azetidinyl)oxy-nitrobenzene

생성물 1

HCID 104759194-(3,3-Diethyl-4-oxo-1-(phenylmethylaminocarbonyl)-2-(R, S)-azetidinyl)oxy-nitrobenzene수율 70%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Triethylamine (1.26 mL, 9.1 mmol), 4-dimethylaminopyridine (20 mg, 0.2 mmol), and benzyl isocyanate (1.12 mL, 9.1 mmol) were successively added to a solution of 4-(3,3-diethyl-4-oxo-2-azetidinyl)oxy-nitrobenzene (1.2 gm, 4.6 mmol) in methylene chloride (10 mL). The solution was stirred at room temperature for 1.5 hours, then ethyl acetate (100 mL) was added. The solution was sucessively washed with 1N hydrochloric acid (3×20 mL), 1N sodium bicarbonate solution (3×20 mL), water (20 mL), and saturated salt solution (20 mL), 1N sodium solution was dried over anhydrous sodium sulfate and the solvent removed by rotoevaporated. The product was purified by flash column chromatography on silica gel eluted with 15% ethyl acetate in hexanes and recrystallized from ethyl acetate/hexanes as a white solid (mp. 96°-97° C.; 1.3 gm, 70% yield): 1H-NMR δ (CDCl3) 1.04 (3H, t, J=7 hz), 1.08 (3H, t, J=7 Hz), 1.76-2.10 (4H, m), 4.47 (2H, d, J=6 hz), 5.76 (1H, s), 7.26-7.44 (7H, m), 8.24 (2H, d, J=9 Hz; ir (thin film) 1780, 1720 cm-1.

후처리

  1. washThe solution was sucessively washed with 1N hydrochloric acid (3×20 mL), 1N sodium bicarbonate solution (3×20 mL), water (20 mL), and saturated salt solution (20 mL), 1N sodium solution
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. customthe solvent removed by rotoevaporated
  4. customThe product was purified by flash column chromatography on silica gel
  5. washeluted with 15% ethyl acetate in hexanes
  6. customrecrystallized from ethyl acetate/hexanes as a white solid (mp. 96°-97° C.; 1.3 gm, 70% yield)

출처 및 근거

ORD 기록
ord-dad84edc1d39432693876bd5cd4b66a3
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229510

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