m-Chloroperbenzoic acid → HCID 178494622, compound

HRID 862488Notes

Reaction equation

HRID 862488 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][CH:23]=[CH:22][N:21]=3)[C:7]=2[CH:26]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:35])C=1>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][CH:23]=[CH:22][N+:21]=3[O-:35])[C:7]=2[CH:26]=1)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54255342HCID 54255342, compound

Product 1

HCID 178494622HCID 178494622, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(-)-(3S,4R)-6-Cyano-3,4-dihydro-2,2-bis(methoxymethyl)-4-(2-pyridylamino)-2H-1-benzopyran-3-ol (152 mg, 0.43 mmol) obtained in Example 42 was dissolved in dichloromethane (5 ml), and m-chloroperbenzoic acid (150 mg, purity 80%) was added under ice-cooling. The mixture was stirred for 1.5 hours. Dichloromethane was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (methanol:chloroform=5:95) to give 94.5 mg of the title compound (59%).

Workup

  1. temperaturecooling
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (methanol:chloroform=5:95)

Sources & evidence

ORD record
ord-31979fcc1dc244ff81b917e03c8194a5
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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