tert-Butyl methyl ether → tert-butyl (R)-4-oxo-2-[4-(2-oxo-2H-pyridin-1-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate

HRID 602331Notes

Reaction equation

HRID 602331 reaction equation
C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[C:19]([N:26]1[CH2:33][C:32](=[O:34])[CH2:31][C@@H:27]1[C:28]([OH:30])=O)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]2=[O:48])=[CH:38][CH:37]=1.COC(C)(C)C>C1(C)C=CC=CC=1>[O:34]=[C:32]1[CH2:33][N:26]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:27]([C:28](=[O:30])[NH:35][C:36]2[CH:41]=[CH:40][C:39]([N:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]3=[O:48])=[CH:38][CH:37]=2)[CH2:31]1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 115356951-(4-Aminophenyl)-1H-pyridin-2-oneHCID 41098094(2R)-1-((tert-butoxy)carbonyl)-4-oxopyrrolidine-2-carboxylic acid

Product 1

HCID 58691233tert-butyl (R)-4-oxo-2-[4-(2-oxo-2H-pyridin-1-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.2 742 mg (3.00 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are added to a suspension of 459 mg (2.00 mmol) of Boc-4-keto-D-proline and 372 mg (2.00 mmol) of 1-(4-aminophenyl)-1H-pyridin-2-one in 25 ml of toluene, and the mixture is stirred at room temperature for 18 hours. 200 ml of tert-butyl methyl ether are added, and the precipitate formed is filtered off. 200 ml of petroleum ether are added to the filtrate, and the resultant precipitate is filtered off, giving tert-butyl (R)-4-oxo-2-[4-(2-oxo-2H-pyridin-1-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate as a brownish solid; ESI 398.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. addition200 ml of petroleum ether are added to the filtrate
  4. filtrationthe resultant precipitate is filtered off

Sources & evidence

ORD record
ord-38b7214b354742bea807f371abc4083f
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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