Dimethyl Sulfoxide → HCID 57254734, compound

HRID 2082620Notes

Reaction equation

HRID 2082620 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([CH:13]1[CH:39]=[C:38]([CH3:40])[CH:37]([F:41])[CH:36]([CH3:42])[CH2:35][CH:34]([O:43][CH3:44])[CH:33]2[O:45][C:29]([OH:49])([CH:30]([CH3:48])[CH2:31][CH:32]2[O:46][CH3:47])[C:28](=[O:50])[C:27](=[O:51])[N:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=[O:52])[O:19][CH:18]([C:53]([CH3:64])=[CH:54][CH:55]2[CH2:60][CH2:59][CH:58]([OH:61])[CH:57]([O:62][CH3:63])[CH2:56]2)[CH:17]([CH3:65])[CH:16]([O:66][Si:67]([CH:74]([CH3:76])[CH3:75])([CH:71]([CH3:73])[CH3:72])[CH:68]([CH3:70])[CH3:69])[CH2:15][C:14]1=[O:77])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([CH:13]1[CH:39]=[C:38]([CH3:40])[CH:37]([F:41])[CH:36]([CH3:42])[CH2:35][CH:34]([O:43][CH3:44])[CH:33]2[O:45][C:29]([OH:49])([CH:30]([CH3:48])[CH2:31][CH:32]2[O:46][CH3:47])[C:28](=[O:50])[C:27](=[O:51])[N:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=[O:52])[O:19][CH:18]([C:53]([CH3:64])=[CH:54][CH:55]2[CH2:60][CH2:59][C:58](=[O:61])[CH:57]([O:62][CH3:63])[CH2:56]2)[CH:17]([CH3:65])[CH:16]([O:66][Si:67]([CH:74]([CH3:76])[CH3:75])([CH:71]([CH3:73])[CH3:72])[CH:68]([CH3:70])[CH3:69])[CH2:15][C:14]1=[O:77])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57141870HCID 57141870, compound

Product 1

HCID 57254734HCID 57254734, compound

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) is added dimethyl sulfoxide (361 mg) dropwise, followed by a solution of 17-ethyl-20-fluoro-1-hydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-14-triisopropylsilyloxy-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 is stirred for 30 min. at -78° C. and then triethylamine (1 ml) is added. The reaction temperature is raised to room temperature, reaction is poured into water (20 ml), 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-cbaead0a0f0a4aca9734d5d781fbe38e
Source dataset
uspto-grants-1993_02
Patent number
US05189042

Reaction notes

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