Dimethyl Sulfoxide → HCID 67195552, compound

HRID 2035409Notes

Reaction equation

HRID 2035409 reaction equation
[H-].[Na+].CS(C)=O.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)CC2C=CC(C[CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=CC=2)C=CC=CC=1.O=[C:45]1[CH2:50][CH2:49][CH2:48][N:47]([CH2:51][CH2:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:46]1.[OH2:60]>>[C:26]1([CH2:25][CH2:24][CH2:23][O:60][C:29]2[CH:30]=[CH:31][C:26]([CH:25]=[C:45]3[CH2:50][CH2:49][CH2:48][N:47]([CH2:51][CH2:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:46]3)=[CH:27][CH:28]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 5

HCID 679Dimethyl Sulfoxide3×HCID 962WaterHCID 24758Sodium hydrideHCID 67198427HCID 67198427, compoundHCID 86635606HCID 86635606, compound

Product 1

HCID 67195552HCID 67195552, compound

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60% in-oil dispersion, 800 mg) was added at room temperature to dimethyl sulfoxide (20 mL) under an argon gas atmosphere. The reaction mixture was stirred at 60° C. for 3 hours. The reaction mixture was cooled at room temperature. From the total obtained solution, 1.3 mL was added at room temperature to a dimethyl sulfoxide solution (2.0 mL) of triphenyl[4-(4-phenylbutyl)benzyl]phosphonium bromide salt (830 mg). The reaction mixture was stirred at room temperature for 30 minutes, and added with a dimethyl sulfoxide (2.0 mL) solution of the compound (830 mg) prepared in Example 24. The reaction mixture was stirred at 50° C. for 18 hours. The mixture was added with water (10 mL), and extracted with diethyl ether. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1), to thereby obtain the title compound (112 mg) having the following physical properties.

Workup

  1. temperatureThe reaction mixture was cooled at room temperature
  2. customFrom the total obtained solution, 1.3 mL
  3. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  4. stirringThe reaction mixture was stirred at 50° C. for 18 hours
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a897daac890741d88bd07b6c0a7c2fae
Source dataset
uspto-grants-2013_11
Patent number
US08575134B2

Reaction notes

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