m-Chloroperbenzoic acid → HCID 10837757, compound

HRID 862485Notes

Reaction equation

HRID 862485 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:15][O:16][CH3:17])([CH2:12][O:13][CH3:14])[C@@H:9]([OH:18])[C@H:8]([NH:19][C:20]3[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:27][CH2:28][S:29][CH3:30])[N:21]=3)[C:7]=2[CH:31]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:40])C=1.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:12][O:13][CH3:14])([CH2:15][O:16][CH3:17])[C@@H:9]([OH:18])[C@H:8]([NH:19][C:20]3[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:27][CH2:28][S:29]([CH3:30])=[O:40])[N:21]=3)[C:7]=2[CH:31]=1)#[N:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10623257HCID 10623257, compound

Product 1

HCID 10837757HCID 10837757, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(-)-(3S,4R)-6-Cyano-3,4-dihydro-4-[(1,6-dihydro-1-(2-methylthioethyl)-6-oxo-3-pyridazinyl)amino]-2,2-bis(methoxymethyl)-2H-1-benzopyran-3-ol (262 mg) obtained in Example 57 was dissolved in dichloromethane (20 ml), and m-chloroperbenzoic acid (152 mg) was added under ice-cooling. The mixture was reacted for 30 minutes. The reaction mixture was poured in a saturated aqueous solution of sodium hydrogen carbonate and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1-20:1) to give 182 mg (65%) and 89 mg (33%) of the title compounds, respectively.

Workup

  1. temperaturecooling
  2. customThe mixture was reacted for 30 minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customto give a residue
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1-20:1)

Sources & evidence

ORD record
ord-7d5f484c3bc2454e85154d59cb61c3f6
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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