Dimethyl Sulfoxide → HCID 57251512, compound

HRID 373282Notes

Reaction equation

HRID 373282 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][CH:63]=[CH2:64])[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][CH:63]=[CH2:64])[CH2:55]2)[CH:17]([CH3:66])[CH:16]([O:67][Si:68]([CH:72]([CH3:74])[CH3:73])([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 86746333HCID 86746333, compound

Product 1

HCID 57251512HCID 57251512, 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"-allyloxycyclohexyl)-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 mixture is allowed to rise to room temperature, 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. customto rise to room temperature
  2. extractionextracted with ethyl acetate (three times)
  3. washCombined organic layers are washed (water, sat'd NaHCO3)
  4. dry with materialdried (anhydrous Na2SO4)
  5. filtrationfiltered
  6. customRemoval of solvent
  7. customfollowed by purification (silica gel column chromatography)

Sources & evidence

ORD record
ord-ffed7bd6a829406cb1626ef10f307a25
Source dataset
uspto-grants-1992_11
Patent number
US05162334

Reaction notes

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