Dimethyl Sulfoxide → HCID 57314607, compound

HRID 247904Notes

Reaction equation

HRID 247904 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]([CH3:63])=[CH:53][CH:54]2[CH2:59][CH2:58][CH:57]([OH:60])[CH:56]([O:61][CH3:62])[CH2:55]2)[CH:17]([CH3:64])[CH:16]([O:65][Si:66]([CH:73]([CH3:75])[CH3:74])([CH:70]([CH3:72])[CH3:71])[CH:67]([CH3:69])[CH3:68])[CH2:15][C:14]1=[O:76])[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]([CH3:63])=[CH:53][CH:54]2[CH2:59][CH2:58][C:57](=[O:60])[CH:56]([O:61][CH3:62])[CH2:55]2)[CH:17]([CH3:64])[CH:16]([O:65][Si:66]([CH:70]([CH3:72])[CH3:71])([CH:73]([CH3:75])[CH3:74])[CH:67]([CH3:69])[CH3:68])[CH2:15][C:14]1=[O:76])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 56974216HCID 56974216, compound

Product 1

HCID 57314607HCID 57314607, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (-78° C.) of oxalyl chloride (1.5 ml of 2M solution in CH2Cl2) was added dimethyl sulfoxide (361 mg) dropwise, followed by a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-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 (947 mg) in dry methylene chloride (3 ml). The reaction mixture was stirred for 30 min. at -78° C. and then triethylamine (1 ml) was added. The reaction temperature was raised to room temperature, reaction was poured into water (20 ml), and extracted with ethyl acetate (three times). The combined organic layers were washed (water, sat'd NaHCO3), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel chromatography, 40% ethyl acetate: 60% hexane) gave 870 mg of title compound.

Workup

  1. temperatureThe reaction temperature was raised to room temperature
  2. customreaction
  3. extractionextracted with ethyl acetate (three times)
  4. washThe combined 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 chromatography, 40% ethyl acetate: 60% hexane)

Sources & evidence

ORD record
ord-a0966bacf79f45739280ebd7a5714703
Source dataset
uspto-grants-1993_05
Patent number
US05208241

Reaction notes

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