Dimethyl Sulfoxide → HCID 59815097, compound

HRID 2382628Notes

Reaction equation

HRID 2382628 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([CH2:20][CH2:21][CH2:22][C@H:23]2[C@H:27](Cl)[CH2:26][C@@H:25]([OH:29])[C@@H:24]2[C:30]2[CH:35]=[CH:34][C:33]([CH:36]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=3)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:32][CH:31]=2)=[CH:18][CH:19]=1)=[O:14].CCN(CC)CC>C(Cl)Cl.O>[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([CH2:20][CH2:21][CH2:22][C@@H:23]2[C@@H:24]([C:30]3[CH:35]=[CH:34][C:33]([CH:36]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=4)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:32][CH:31]=3)[C:25](=[O:29])[CH:26]=[CH:27]2)=[CH:18][CH:19]=1)=[O:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59815109HCID 59815109, compound

Product 1

HCID 59815097HCID 59815097, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of DMSO (120 μL, 1.69 mmol) in 1 mL CH2Cl2 was added to a −78° C. solution of oxalyl chloride in CH2Cl2 (400 μL, 0.80 mmol, 2 M), rinsing with 1 mL CH2Cl2. The reaction was stirred at −78° C. for 30 min. and then a solution of 5 (297 mg, 0.49 mmol) in 1.2 mL CH2Cl2 was added dropwise by cannula, rinsing with 1.2 mL. Et3N (400 μL, 2.9 mmol) was added and the reaction was allowed to warm to room temperature. After 5 h, 60 mL H2O was added and the resulting mixture was extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (0%→100% ethyl acetate/hexanes) to give compound 6 (276 mg, 99%).

Workup

  1. washrinsing with 1 mL CH2Cl2
  2. washrinsing with 1.2 mL
  3. temperatureto warm to room temperature
  4. waitAfter 5 h
  5. extractionthe resulting mixture was extracted with CH2Cl2 (3×50 mL)
  6. washThe combined CH2Cl2 solution was washed with brine
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica gel (0%→100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bd521118f2b44df2b1a3f647a5382df1
Source dataset
uspto-grants-2012_09
Patent number
US08263593B2

Reaction notes

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