Dimethyl Sulfoxide → HCID 131722001, compound

HRID 1954031Notes

Reaction equation

HRID 1954031 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][CH2:12][C@H:13]1[C:43](=[O:44])[CH2:42][C@H:41]([OH:45])[C@@H:40]([CH3:46])[C@@H:39](/[C:47](/[CH3:58])=[CH:48]/[C@H:49]2[CH2:54][C@@H:53]([O:55][CH3:56])[C@H:52]([OH:57])[CH2:51][CH2:50]2)[O:38][C:36](=[O:37])[C@H:35]2[N:30]([CH2:31][CH2:32][CH2:33][CH2:34]2)[C:28](=[O:29])[C:26](=[O:27])[C@:24]2([OH:59])[O:25][C@@H:20]([C@@H:21]([O:61][CH3:62])[CH2:22][C@H:23]2[CH3:60])[C@@H:19]([O:63][CH3:64])[CH2:18][C@@H:17]([CH3:65])[CH2:16][C:15]([CH3:66])=[CH:14]1.C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH2:12]([C@@H:13]1[CH:14]=[C:15]([CH3:66])[CH2:16][C@H:17]([CH3:65])[CH2:18][C@H:19]([O:63][CH3:64])[C@H:20]2[O:25][C@:24]([OH:59])([C@H:23]([CH3:60])[CH2:22][C@@H:21]2[O:61][CH3:62])[C:26](=[O:27])[C:28](=[O:29])[N:30]2[C@@H:35]([CH2:34][CH2:33][CH2:32][CH2:31]2)[C:36](=[O:37])[O:38][C@H:39](/[C:47](/[CH3:58])=[CH:48]/[C@@H:49]2[CH2:50][CH2:51][C:52](=[O:57])[C@H:53]([O:55][CH3:56])[CH2:54]2)[C@H:40]([CH3:46])[C@@H:41]([OH:45])[CH2:42][C:43]1=[O:44])[CH3:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5282071Immunomycin

Product 1

HCID 131722001HCID 131722001, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Methylsulfide-chlorine complex was prepared by adding oxalyl chloride (0.32 g) into a solution of dimethylsulfoxide (0.44 g) in 4 mL of methylene chloride and stirred at -70° C. for 30 minutes. The solution of the complex was slowly added to a stirred solution of ascomycin (1.6 g) in 5 mL of methylene chloride at -70° C. After stirring for 30 minutes, triethylamine (1.4 g) was added and the mixture was allowed to stir for an additional 30 minutes at -70° C. The reaction mixture was then allowed to warm to room temperature followed by additional stirring for 1 hour. The reaction mixture was diluted with 100 mL of ether, washed with 1N-HCl aq. solution (30 mL×2), brine (30 mL), dried over magnesium sulfate anhydrous, and the solvent removed in vacuo. The crude product was purified on 70 gram of silica gel, eluting with ether to obtain 0.95 g of the title compound.

Workup

  1. customMethylsulfide-chlorine complex was prepared
  2. stirringAfter stirring for 30 minutes
  3. stirringto stir for an additional 30 minutes at -70° C
  4. temperatureto warm to room temperature
  5. stirringby additional stirring for 1 hour
  6. washwashed with 1N-HCl aq. solution (30 mL×2), brine (30 mL)
  7. dry with materialdried over magnesium sulfate anhydrous
  8. customthe solvent removed in vacuo
  9. customThe crude product was purified on 70 gram of silica gel
  10. washeluting with ether

Sources & evidence

ORD record
ord-6848ebff6d534c9fb21533654e1fa263
Source dataset
uspto-grants-2000_09
Patent number
US06121257

Reaction notes

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