Sodium Thiosulfate → HCID 53321225, compound

HRID 2042945Notes

Reaction equation

HRID 2042945 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17]SC)[O:9]2)=[CH:4][C:3]=1[CH2:20][C:21]1[S:22][C:23]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)=[CH:24][N:25]=1.Cl[C:32]1C=C(C=CC=1)C(OO)=O.[S:42]([O-:46])([O-])(=[O:44])=S.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][S:42]([CH3:32])(=[O:46])=[O:44])[O:9]2)=[CH:4][C:3]=1[CH2:20][C:21]1[S:22][C:23]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)=[CH:24][N:25]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 53317310HCID 53317310, compound

Product 1

HCID 53321225HCID 53321225, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of methyl sulfide 92 (175 mg, 0.37 mmol) and meta-chloroperoxybenzoic acid (210 mg 0.93 mmol) in CH2Cl2 (3.7 mL) was stirred at 0° C. for 1 h. To the reaction solution was added to sodium thiosulfate solution, and the resulting mixture was extracted with CH2Cl2. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and brine, and dried with anhydrous MgSO4. The drying agent was filtered off, and evaporated under reduced pressure. The residue was purified by prep HPLC (C18) to afford the titled compound methylsulfone 93 (121 mg, 66%) as a solid.

Workup

  1. extractionthe resulting mixture was extracted with CH2Cl2
  2. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried with anhydrous MgSO4
  4. filtrationThe drying agent was filtered off
  5. customevaporated under reduced pressure
  6. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-0d26aa1e1a764776ab3c7543290a2e63
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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