Dimethyl Sulfoxide → HCID 57248286, compound

HRID 257700Notes

Reaction equation

HRID 257700 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([CH:13]1[CH:39]=[C:38]([CH3:40])[CH2:37][CH:36]([CH3:41])[CH2:35][CH:34]([O:42][CH3:43])[CH:33]2[O:44][C:29]([OH:48])([CH:30]([CH3:47])[CH2:31][CH:32]2[O:45][CH3:46])[C:28](=[O:49])[C:27](=[O:50])[N:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=[O:51])[O:19][CH:18]([C:52]([CH3:68])=[CH:53][CH:54]2[CH2:59][CH2:58][CH:57]([OH:60])[CH:56]([O:61][C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[CH2:55]2)[CH:17]([CH3:69])[CH:16]([O:70][Si:71]([CH:78]([CH3:80])[CH3:79])([CH:75]([CH3:77])[CH3:76])[CH:72]([CH3:74])[CH3:73])[CH2:15][C:14]1=[O:81])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([CH:13]1[CH:39]=[C:38]([CH3:40])[CH2:37][CH:36]([CH3:41])[CH2:35][CH:34]([O:42][CH3:43])[CH:33]2[O:44][C:29]([OH:48])([CH:30]([CH3:47])[CH2:31][CH:32]2[O:45][CH3:46])[C:28](=[O:49])[C:27](=[O:50])[N:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=[O:51])[O:19][CH:18]([C:52]([CH3:68])=[CH:53][CH:54]2[CH2:59][CH2:58][C:57](=[O:60])[CH:56]([O:61][C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[CH2:55]2)[CH:17]([CH3:69])[CH:16]([O:70][Si:71]([CH:78]([CH3:80])[CH3:79])([CH:72]([CH3:74])[CH3:73])[CH:75]([CH3:77])[CH3:76])[CH2:15][C:14]1=[O:81])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57285756HCID 57285756, compound

Product 1

HCID 57248286HCID 57248286, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (-78° C.) of oxalyl chloride is added dimethyl sulfoxide dropwise, followed by a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-3"-phenoxycyclohexyl)-1'-methylvinyl]-14-triisopropylsiloxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone in dry methylene chloride. The reaction mixture is stirred for 30 min. at -78° C. and then triethylamine is added. The reaction temperature is raised to room temperature, reaction was poured into water, and extracted with ethyl acetate (three times). Combined organic layers are washed (water, sat'd NaHCO3), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel column chromatography) gives the title compound.

Workup

  1. temperatureThe reaction temperature is raised to room temperature
  2. customreaction
  3. extractionextracted with ethyl acetate (three times)
  4. washCombined organic layers are washed (water, sat'd NaHCO3)
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. customRemoval of solvent
  8. customfollowed by purification (silica gel column chromatography)

Sources & evidence

ORD record
ord-df2554874e644a0c80a867a30e491bf7
Source dataset
uspto-grants-1993_11
Patent number
US05262533

Reaction notes

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