Dimethyl Sulfoxide → HCID 86746820, compound

HRID 248285Notes

Reaction equation

HRID 248285 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]([CH3:65])=[CH:53][CH:54]2[CH2:59][CH2:58][CH:57]([OH:60])[CH:56]([O:61][CH2:62][CH2:63][CH3:64])[CH2:55]2)[CH:17]([CH3:66])[CH:16]([O:67][Si:68]([CH:75]([CH3:77])[CH3:76])([CH:72]([CH3:74])[CH3:73])[CH:69]([CH3:71])[CH3:70])[CH2:15][C:14]1=[O:78])[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]([CH3:65])=[CH:53][CH:54]2[CH2:59][CH2:58][C:57](=[O:60])[CH:56]([O:61][CH2:62][CH2:63][CH3:64])[CH2:55]2)[CH:17]([CH3:66])[CH:16]([O:67][Si:68]([CH:72]([CH3:73])[CH3:74])([CH:69]([CH3:71])[CH3:70])[CH:75]([CH3:77])[CH3:76])[CH2:15][C:14]1=[O:78])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86746821HCID 86746821, compound

Product 1

HCID 86746820HCID 86746820, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (-78° C.) of oxalyl chloride added dimethyl sulfoxide dropwise, followed by a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-3"-propyloxycyclohexyl)-1'-methylvinyl]-14-triisopropylsiloxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos18-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 were 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 were 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-b7f6a749c31c45fabff5ab6323907746
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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