4-Methylmorpholine → N-(4-chlorophenyl)-(R)-1-{2-[4-(3-oxomorpholin-4-yl)phenyl]acetyl}pyrrolidine-2-carboxamide

HRID 1091271Notes

Reaction equation

HRID 1091271 reaction equation
CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[Cl-].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C@H:31]2[CH2:35][CH2:34][CH2:33][NH2+:32]2)=[O:30])=[CH:24][CH:23]=1.[O:36]=[C:37]1[CH2:42][O:41][CH2:40][CH2:39][N:38]1[C:43]1[CH:48]=[CH:47][C:46]([CH2:49][C:50](O)=[O:51])=[CH:45][CH:44]=1>CN(C=O)C.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29]([C@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:50](=[O:51])[CH2:49][C:46]2[CH:45]=[CH:44][C:43]([N:38]3[CH2:39][CH2:40][O:41][CH2:42][C:37]3=[O:36])=[CH:48][CH:47]=2)=[O:30])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 586912414-(3-Oxomorpholin-4-yl)phenylacetic acidHCID 86607080(R)-2-(4-chlorophenylcarbamoyl)pyrrolidinium chloride

Product 1

HCID 58691223N-(4-chlorophenyl)-(R)-1-{2-[4-(3-oxomorpholin-4-yl)phenyl]acetyl}pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.26 ml (2.4 mmol) of 4-methylmorpholine and 230 mg (1.2 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) are added to a solution of 261 mg (1.00 mmol) of (R)-2-(4-chlorophenyl-carbamoyl)pyrrolidinium chloride and 235 mg (1.00 mmol) of 4-(3-oxomorpholin-4-yl)phenylacetic acid in 2 ml of DMF, and the mixture is stirred at room temperature for 18 hours. The reaction mixture is introduced into water, and the precipitate formed is filtered off, giving N-(4-chlorophenyl)-(R)-1-{2-[4-(3-oxomorpholin-4-yl)phenyl]acetyl}pyrrolidine-2-carboxamide as a slightly brownish solid; ESI 442.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-ee2df718879c496b86a46e4e026ea7f7
Source dataset
uspto-grants-2012_03
Patent number
US08129373B2

Reaction notes

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