Dimethyl Sulfoxide → HCID 86634387, compound

HRID 1191294Notes

Reaction equation

HRID 1191294 reaction equation
[N:1]1([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C@H:16]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:17]3[CH2:28][CH2:29][CH2:30][OH:31])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS(C)=O.C(N(CC)CC)C.O>ClCCl>[N:1]1([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C@H:16]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C@@H:17]3[CH2:28][CH2:29][CH:30]=[O:31])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 86634388HCID 86634388, compound

Product 1

HCID 86634387HCID 86634387, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 39 (174 mg), dimethylsulphoxide (3 mL) and triethylamine (1.5 mL) in dichloromethane (3 mL) with stirring, sulfur trioxide pyridine complex (212 mg) was added into the solution at room temperature. The reaction solution was stirred for 2 hours, added water and extracted with a mixture solution of hexane/ethyl acetate. The extract was washed with water, aqueous 5% potassium bisulfate solution, water and saturated brine, dried over anhydrous magnesium sulfate, concentrated and obtained the title compound (171 mg) having the following physical properties.

Workup

  1. additionsulfur trioxide pyridine complex (212 mg) was added into the solution at room temperature
  2. extractionextracted with a mixture solution of hexane/ethyl acetate
  3. washThe extract was washed with water, aqueous 5% potassium bisulfate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f4f403ec59b4215846e9bc7729f1ee3
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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