Pyridine → 2-N-[(4-chlorophenyl)]-1-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(R)-pyrrolidine-1,2-dicarboxamide
Reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].N1C=CC=CC=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][C:28]2=[O:33])=[CH:23][CH:22]=1.[Cl-].[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][C:43]([C@H:45]2[CH2:49][CH2:48][CH2:47][NH2+:46]2)=[O:44])=[CH:38][CH:37]=1.C(N(C(C)C)C(C)C)C>ClCCl>[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([NH:42][C:43]([C@H:45]2[CH2:49][CH2:48][CH2:47][N:46]2[C:2]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][C:28]3=[O:33])=[CH:25][CH:26]=2)=[O:3])=[O:44])=[CH:40][CH:41]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
1.01 g (5.00 mmol) of 4-nitrophenyl chloroformate and 0.404 ml (5.00 mmol) of pyridine are added to a solution of 961 mg (5.00 mmol) of 4-(4-aminophenyl)morpholin-3-one in 10 ml of dichloromethane, and the mixture is stirred at room temperature for 1 hour. 1.31 g (5.00 mmol) of (R)-2-(4-chlorophenylcarbamoyl)pyrrolidinium chloride and 2.55 ml (15.0 mmol) of N-ethyldiisopropylamine are added to the suspension. The reaction mixture is stirred at room temperature for 12 hours and then evaporated, and the residue is chromatographed on a silica-gel column, giving 2-N-[(4-chlorophenyl)]-1-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(R)-pyrrolidine-1,2-dicarboxamide as a yellowish solid, ESI 443.
Workup
- stirringThe reaction mixture is stirred at room temperature for 12 hours
- customevaporated
- customthe residue is chromatographed on a silica-gel column
Sources & evidence
- ORD record
- ord-ed081a49f55f4891b077586b2386f266
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906516B2
Reaction notes
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