m-Chloroperbenzoic acid → HCID 20034625, compound

HRID 231162Notes

Reaction equation

HRID 231162 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]([N:11]2[C:15]3=[CH:16][S:17][CH:18]=[C:14]3[N:13]=[C:12]2[S:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=2)=[O:10])=[CH:5][CH:4]=1.[OH:30]P([O-])(O)=O.[K+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[C:15]3=[CH:16][S:17][CH:18]=[C:14]3[N:13]=[C:12]2[S:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=2)=[O:30])=[O:10])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516951Monobasic potassium phosphateHCID 20034621HCID 20034621, compound

Product 1

HCID 20034625HCID 20034625, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

850 mg (2 mmol) of the title compound from Example 21 were dissolved in 50 ml of CH2Cl2, and 50 ml of aqueous Na2HPO4 /KH2PO4 buffer solution (pH 7.5; 7.4 ml of KH2PO4 solution (45.35 g/l)+42.5 ml of Na2HPO4 solution (59.5 g/l) were added. While stirring vigorously at room temperature, 500 mg (2.5 mmol) of m-chloroperbenzoic acid dissolved in CH2Cl2 were added dropwise. The organic phase was dried over MgSO4 and concentrated, and the residue was chromatographed on silica gel using ethyl acetate. The title compound crystallized from isopropanol. Melting point 119°-120° C.

Workup

  1. additionwere added dropwise
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue was chromatographed on silica gel
  5. customThe title compound crystallized from isopropanol

Sources & evidence

ORD record
ord-77fd0135f90a47b7bf4a613b8135420c
Source dataset
uspto-grants-1989_07
Patent number
US04845118

Reaction notes

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