Benzoyl chloride → (3R,4S)-1-BENZOYL-4-PHENYL-3-[(TRIETHYLSILYL)OXY]-2-AZETIDINONE

HRID 327353Notes

Reaction equation

HRID 327353 reaction equation
[C:1]1([C@@H:7]2[NH:10][C:9](=[O:11])[C@@H:8]2[O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:29]([N:10]1[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@@H:8]([O:12][Si:13]([CH2:16][CH3:17])([CH2:18][CH3:19])[CH2:14][CH3:15])[C:9]1=[O:11])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 10826417(3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one

Product 1

HCID 10500068(3R,4S)-1-BENZOYL-4-PHENYL-3-[(TRIETHYLSILYL)OXY]-2-AZETIDINONE

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (3R, 4S)-4-phenyl-3-triethylsilyloxy-2-azetidinone (LXXII) (1.000 g, 3.601 mmol) in dry CH2Cl2 (25 mL) was added N,N-diisopropylethylamine (0.689 mL, 3.961 mmol, 1.1 equiv) at 0° C. under an argon atmosphere. The solution was stirred for 5 min followed by the addition of benzoyl chloride (0.459 mL, 3.961 mmol, 1.1 equiv) and 4-dimethylaminopyridine (96.5 mg, 0.790 mmol, 0.20 equiv). The reaction mixture was stirred at room temperature for 1 h, then it was diluted with ethyl acetate (25 mL). The resulting solution was washed with brine, 10% NaHCO3, 10% HCl solution, dried (MgSO4), and concentrated to give a crude compound as an oil. The compound was further purified by silica gel flash chromatography (being eluted with 15% ethyl acetate in hexanes) which afforded 1.04 g (Y: 80%) of 8.07-8.00 (m, 2H) 7.59-7.45 (m, 3H) 7.37-7.31 (m, 5H) 5.41 (d, J=6.1 Hz, 1H) 0.83-0.77 (m, 9H) 0.54-0.42 (m, 6H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. washThe resulting solution was washed with brine, 10% NaHCO3, 10% HCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a crude compound as an oil
  6. customThe compound was further purified by silica gel flash chromatography (being eluted with 15% ethyl acetate in hexanes) which
  7. customafforded 1.04 g (Y: 80%) of 8.07-8.00 (m, 2H) 7.59-7.45 (m, 3H) 7.37-7.31 (m, 5H) 5.41 (d, J=6.1 Hz, 1H) 0.83-0.77 (m, 9H) 0.54-0.42 (m, 6H)

Sources & evidence

ORD record
ord-1c94892ee9624caebd60ee8130694831
Source dataset
uspto-grants-1993_12
Patent number
US05272171

Reaction notes

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