m-Chloroperbenzoic acid → HCID 14013758, compound

HRID 255414Notes

Reaction equation

HRID 255414 reaction equation
[CH2:1]([S:3][C:4]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[N:7]=[C:6]([C:18]([F:21])([F:20])[F:19])[C:5]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:35])C=1>C(Cl)Cl>[CH2:1]([S:3]([C:4]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:14]([F:15])([F:16])[F:17])[N:7]=[C:6]([C:18]([F:21])([F:19])[F:20])[C:5]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:35])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14013757HCID 14013757, compound

Product 1

HCID 14013758HCID 14013758, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4.8 g (0.012 mol) of product of Example 33 in 30 ml of CH2Cl2 was added 4.08 g (0.024 mol) of MCPBA. The reaction was monitored by TLC. The reaction mixture was filtered, washed with NaHCO3, dried (MgSO4) and concentrated in vacuo to give 4.56 g of solid which was purified by HPLC using 8% ethyl acetate/cyclohexane to elute the first fraction (1.52 g) followed by 15% ethyl acetate/cyclohexane to elute 1.46 g of the desired product. Recrystallization of the 1.46 g solid in hot hexane afforded 0.88 g (17.4%) of product as a white solid; mp 87°-88.5° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91c2febe3a3a47e495b3b3f8b7f79d13
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Reaction notes

Loading…