m-Chloroperbenzoic acid → HCID 86754921, compound

HRID 2270491Notes

Reaction equation

HRID 2270491 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([NH:19][CH:20]=[CH:21][CH3:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:1]([NH:11][C@H:12]([C:17]([NH:19][CH:20]1[O:31][CH:21]1[CH3:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70008891HCID 70008891, compound

Product 1

HCID 86754921HCID 86754921, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-(Cbz-leucinyl)-amino-propene (2.95 g, 9.7 mmol) was dissolved in methylene chloride (100 ml), then mCPBA (5.0 g, 29.1 mmol) was added and the reaction was stirred overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, extracted with EtOAc, dried with magnesium sulfate, filtered, concentrated, and chromatographed (silica gel, 50% EtOAc: hexanes).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 50% EtOAc: hexanes)

Sources & evidence

ORD record
ord-84b90e53ed8f4d65aa45a57a823490c4
Source dataset
uspto-grants-2001_12
Patent number
US06331542B1

Reaction notes

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