Dimethylformamide → (S)-4-Benzyl-2-oxazolidinone
Reaction equation
C(Cl)(=O)C(Cl)=O.C([C:9]1[CH:10]=[C:11](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)[CH:12]=[CH:13][CH:14]=1)#N.C[N:21]([CH:23]=[O:24])C>ClCCl>[CH2:15]([C@H:16]1[CH2:17][O:19][C:23](=[O:24])[NH:21]1)[C:11]1[CH:10]=[CH:9][CH:14]=[CH:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Oxalyl chloride was slowly added at room temperature to a mixture of (2E)-3-(3-cyanophenyl)acrylic acid, DMF and dichloromethane and stirred for 30 minutes. The reaction solution was concentrated under a reduced pressure, and the thus obtained residue was dissolved in THF and again concentrated under a reduced pressure. By repeating this operation, excess hydrogen chloride and oxalyl chloride were removed and crude (2E)-3-(3-cyanophenyl)acrylic acid chloride was obtained. The thus obtained crude product and (S)-4-benzyl-2-oxazolidinone were subjected to condensation reaction in the same manner as in Reference Example 1 to obtain 3-{(1E)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxoprop-1-en-1-yl}benzonitrile. FP: 333, NMR 1: 3.02 (1H, dd, J=7.0, 13.5 Hz), 3.10 (1H, dd, J=3.5, 13.5 Hz), 4.25 (1H, dd, J=3.0, 8.5 Hz), 4.41 (1H, t, J=8.5 Hz), 4.75-4.85 (1H, m), 7.20-7.37 (5H, m), 7.68 (1H, t, J=8.0 Hz), 7.85 (2H, br.s), 7.90-7.95 (1H, m), 8.01-8.06 (1H, m), 8.20 (1H, br.s).
Workup
- concentrationThe reaction solution was concentrated under a reduced pressure
- dissolutionthe thus obtained residue was dissolved in THF
- concentrationagain concentrated under a reduced pressure
- customwere removed
- customcrude (2E)-3-(3-cyanophenyl)acrylic acid chloride was obtained
Sources & evidence
- ORD record
- ord-c8df1ef17e1a41a9864062aac9f69a9c
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585886B2
Reaction notes
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