m-Chloroperbenzoic acid → HCID 57683185, compound

HRID 2427291Notes

Reaction equation

HRID 2427291 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1([S:26][CH3:27])[CH2:23][C:22]1([F:25])[F:24].ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1([S:26]([CH3:27])=[O:33])[CH2:23][C:22]1([F:24])[F:25]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15979494HCID 15979494, compound

Product 1

HCID 57683185HCID 57683185, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 74 (100 mg, 0.23 mmol) in dichloromethane (5 ml) was added 3-chloroperoxybenzoic acid (77%, 53 mg, 0.25 mmol). The reaction mixture was stirred at room temperature for 18 h, diluted with dichloromethane (10 ml) and washed with saturated aqueous sodium hydrogencarbonate solution (2×5 ml). The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The residue was dissolved in acetonitrile/dimethyl sulphoxide (1:1, 1 ml) and purified by automated preparative liquid chromatography (Gilson system, 250 mm×30 mm Phenomenex LUNA C18(2) 101m column) using an acetonitrile:water gradient [45:55 to 95:5]. The appropriate fractions were concentrated in vacuo to give the titled compound (9 mg) and a second diastereoisomer, Example 126

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution (2×5 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in acetonitrile/dimethyl sulphoxide (1:1, 1 ml)
  6. custompurified
  7. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-b78abf52d6f54e8d8dff63e90e789794
Source dataset
uspto-grants-2011_06
Patent number
US07968584B2

Reaction notes

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