Dimethyl Sulfoxide → HCID 22104461, compound

HRID 1457328Notes

Reaction equation

HRID 1457328 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][S:6][CH2:5][N:4]1[C:8]([C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9].CS(C)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.C(N(CC)CC)C>C(Cl)Cl>[CH:2]([CH:3]1[CH2:7][S:6][CH2:5][N:4]1[C:8]([C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:9])=[O:1]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 22104504HCID 22104504, compound

Product 1

HCID 22104461HCID 22104461, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.1 g (3.1 mmol) of the title compound of Example 4 was oxidized as described in Example 2 using 1.1 ml (15 mmol) DMSO, 1.9 ml (12.4 mmol) TFAA, 2.2 ml (16 mmol) triethylamine in 25 ml methylene chloride. The crude product was chromatographed on silica gel with chloroform as the eluant to yield 0.3 g of material which was triturated with hot diisopropyl ether to yield 10 mg (1%) crystalline title product. 1H NMR (CDCl3) δ: 9.60(s); 9.30(s,1H); 7.15-7.60(m,10H); 4.10-5.20(m,8H). High Resolution Mass Spectrum: 326.1147±5.8 ppm (C18H18N2O2S).

Workup

  1. customThe crude product was chromatographed on silica gel with chloroform as the eluant

Sources & evidence

ORD record
ord-122f2d2e930e42bf98fd31964adee0c1
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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