Dimethyl Sulfoxide → HCID 13020719, compound

HRID 1680679Notes

Reaction equation

HRID 1680679 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[C@@H:10]([CH3:23])[C:11]([CH3:22])([CH3:21])[C@H:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:24][CH3:25])[CH:4]=[CH:5]2.CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[C@@H:10]([CH3:23])[C:11]([CH3:22])([CH3:21])[C:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:24][CH3:25])[CH:4]=[CH:5]2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9845Trifluoroacetic anhydrideHCID 13020711HCID 13020711, compound

Product 1

HCID 13020719HCID 13020719, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 6b (710 mg, 2 mmole) in CH2Cl2 (10 ml) was oxidized using DMSO (0.35 ml. 5 mmole) and trifluoroacetic anhydride (0.70 ml, 3.75 mmole) in methylene chloride (CH2Cl2) (8 ml) at -65° as described above. After the addition of TEA (1 ml), workup gave a residue which was purified by chromatography to give 474 mg (67%) of 7b as a glass whose structure was confirmed by NMR. This material was converted to the HCl salt which crystallized from methanol-ethyl acetate (MeOH-EtOAc) to give analytically pure 7b.HCl, mp 246°-248° which was confirmed by elemental analysis.

Workup

  1. customat -65°
  2. customgave a residue which
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-ae7adb129c0749268c6c56d8fbcca97e
Source dataset
uspto-grants-1981_06
Patent number
US04275205

Reaction notes

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