m-Chloroperbenzoic acid → HCID 10110323, compound

HRID 1838012Notes

Reaction equation

HRID 1838012 reaction equation
[OH:1][C@H:2]([C:16]1[S:17][C:18]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[OH:1][C@H:2]([C:16]1[S:17][C:18]([C:21]2[CH:22]=[N+:23]([O-:35])[CH:24]=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 9947211HCID 9947211, compound

Product 1

HCID 10110323HCID 10110323, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (4R,5R)-5-{(1S)-hydroxy[5-(3-pyridinyl)-2-thienyl]methyl}-1-methyl-4-phenyl-2-pyrrolidinone (Example 3b, 0.20 g, 0.55 mmol) in CHCl3 (10 mL) was added mCPBA (0.35 g, 1.4 mmol). The reaction mixture was stirred for 40 min, then was treated with a saturated NaHCO3 solution (10 mL). The organic layer was dried (Na2SO4) and was allowed to stand overnight. The white precipitate was filtered off, the filtrate was concentrated under reduced pressure. The crude product was triturated (Et2O/CH2Cl2) to give (4R,5R)-5-{(S)-hydroxy[5-(1-oxido-3-pyridinyl)-2-thienyl]methyl}-1-methyl-4-phenyl 2-pyrrolidinone: mp 138-140° C.; TLC (10% MeOH/CH2Cl2) Rf 0.20; ES-LRMS m/z 381 (MH+).

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. waitto stand overnight
  3. filtrationThe white precipitate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was triturated (Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-8ed8bd3f25bf4c59a8abc577526c5f75
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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