Dimethyl Sulfoxide → HCID 136377640, compound

HRID 1791097Notes

Reaction equation

HRID 1791097 reaction equation
[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]=[CH:17]2)[C@H:13]([OH:27])[CH2:12]1)([O:4][P:5]([OH:8])([OH:7])=[O:6])(=[O:3])[OH:2].[CH3:28]S(C)=O.CN(C=O)C.CI>O>[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]([CH3:28])[CH2:17]2)[C@H:13]([OH:27])[CH2:12]1)([O:4][P:5]([OH:7])([OH:8])=[O:6])(=[O:2])[OH:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 136377641HCID 136377641, compound

Product 1

HCID 136377640HCID 136377640, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 5 (34 mg, 0.055 mmol) was mixed with 1 mL of dimethylsulfoxide, 1 mL of DMF, and 100 μL of methyl iodide at room temperature. After 3 h the reaction mixture was treated with 30 mL of cold water and extracted three times with 10-mL portions of diethyl ether. After neutralization with NaHCO3, chromatographic separation of the aqueous phase on DEAE-Sephadex, using a linear gradient of 0 to 0.8 M TEAB, gave Compound 7 (yield: 10 mg, 28%).

Workup

  1. extractionextracted three times with 10-mL portions of diethyl ether
  2. customAfter neutralization with NaHCO3, chromatographic separation of the aqueous phase on DEAE-Sephadex

Sources & evidence

ORD record
ord-0b53857d38af4d8296b902528530f856
Source dataset
uspto-grants-2006_07
Patent number
US07074596B2

Reaction notes

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