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

HRID 484194Notes

Reaction equation

HRID 484194 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dad84edc1d39432693876bd5cd4b66a3
Source dataset
uspto-grants-1993_07
Patent number
US05229510

Reaction notes

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