HCID 9912033, compound → HCID 11178578, compound

HRID 602339Notes

Reaction equation

HRID 602339 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([N:22]2[CH2:26][C@H:25]([OH:27])[CH2:24][C@@H:23]2[C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][C:38]3=[O:43])=[CH:33][CH:32]=2)=[O:29])=[O:21])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([N:22]2[CH2:26][C:25](=[O:27])[CH2:24][C@@H:23]2[C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][C:38]3=[O:43])=[CH:33][CH:32]=2)=[O:29])=[O:21])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 9912033HCID 9912033, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11178578HCID 11178578, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.21 g (0.98 mmol) of pyridinium chlorochromate (PCC) is added to the solution of 0.3 g (0.65 mmol) of 1-N-[(4-chlorophenyl)]-2-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(1R,4R)-4-hydroxypyrrolidine-1,2-dicarboxamide (Example 7) in 15 ml of methylene chloride, and the reaction mixture is stirred at room temperature for 48 hours. The precipitate is subsequently filtered off, and the filtrate is washed three times with 20 ml of water each time and dried over sodium sulfate. After the solvent has been stripped off, the residue is purified by preparative HPLC, giving 140 mg (47%) of 1-N-[(4-chlorophenyl)]-2-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(R)-4-oxopyrrolidine-1,2-dicarboxamide as a white powder, ESI 457, m.p. 154°.

Workup

  1. filtrationThe precipitate is subsequently filtered off
  2. washthe filtrate is washed three times with 20 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-32f105ed498e497c9969a06002ee92f1
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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