Triethylamine → N-((5S)-3-(4-(1-Methylsulfonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxo-oxazolidin-5-ylmethyl)acetamide
Reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]3=[O:35])=[CH:21][CH:20]=2)=[CH:15][CH2:14]1>ClCCl>[CH3:8][S:9]([N:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]3=[O:35])=[CH:21][CH:20]=2)=[CH:15][CH2:14]1)(=[O:11])=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylamine (253 mg), followed by a solution of methanesulfonyl chloride (69 mg) in dichloromethane (1 ml) was added, with ice-bath cooling, to a stirred suspension of N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide (215 mg, Example 2) in dichloromethane (10 ml). TLC showed complete reaction after 2 hours. The reaction mixture was washed with 2N. HCl, water, saturated sodium hydrogen carbonate and brine. The organic phase was dried over anhydrous sodium sulfate and evaporated to give the title compound as a crystalline solid which was recrystallised from acetonitrile (yield=117 mg, 60%).
Workup
- additionwas added, with ice-bath
- customreaction after 2 hours
- washThe reaction mixture was washed with 2N
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-2d297383ca854471a17900bfcfaed1f8
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365751B1
Reaction notes
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