m-Chloroperbenzoic acid → HCID 22022962, compound

HRID 1793672Notes

Reaction equation

HRID 1793672 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][CH:17]([CH2:19][O:20][C:21]3[CH:25]=[CH:24][O:23][N:22]=3)[O:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.ClC1C=C(C=CC=1)C(OO)=[O:31].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][CH:17]([CH2:19][O:20][C:21]3[CH:25]=[CH:24][O:23][N:22]=3)[O:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11](=[O:31])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 22022987HCID 22022987, compound

Product 1

HCID 22022962HCID 22022962, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (5RS)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (174 mg, 0.48 mM) in dichloromethane (5 ml) was added dropwise a solution of 3-chloroperoxybenzoic acid (80%, 124 mg, 0.57 mM) in dichloromethane (5 ml) at ambient temperature, and stirring continued for 1 hour. Aqueous sodium metabisulfite (5%, 5 ml) was added, and after stirring for 5 minutes the organic phase was separated. After further extraction with dichloromethane (2×10 ml), the combined extracts were washed with aqueous sodium bicarbonate solution (2×15 ml) and dried (magnesium sulfate). Crude product was chromatographed on a 10 g silica Mega Bond Elut® column, eluting first with a gradient from 0–50% ethyl acetate in dichloromethane (to remove sulfone, 10 mg), then with a gradient from 0–2.5% methanol in dichloromethane. Relevant fractions were combined to give the desired product (128 mg).

Workup

  1. stirringafter stirring for 5 minutes the organic phase
  2. customwas separated
  3. extractionAfter further extraction with dichloromethane (2×10 ml)
  4. washthe combined extracts were washed with aqueous sodium bicarbonate solution (2×15 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customCrude product was chromatographed on a 10 g silica Mega Bond Elut® column
  7. washeluting first with a gradient from 0–50% ethyl acetate in dichloromethane (to remove sulfone, 10 mg)

Sources & evidence

ORD record
ord-f4983ebb30254a8bb699350094bd6137
Source dataset
uspto-grants-2006_07
Patent number
US07081538B1

Reaction notes

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