m-Chloroperbenzoic acid → HCID 86754921, compound

HRID 1356526Notes

Reaction equation

HRID 1356526 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-dda7f81ceeb54c81827ddcf89f2710b6
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

Loading…