Dimethyl Sulfoxide → HCID 86701117, compound

HRID 1396279Notes

Reaction equation

HRID 1396279 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:14][C@@H:15]1[C@@H:23]([C@@H:24]([OH:26])[CH3:25])[O:22][C@H:21]2[C@H:17]([N:18]=[C:19]([N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[S:20]2)[C@H:16]1[O:36][CH2:37][CH:38]=[CH2:39])[CH:12]=[CH2:13].C(N(CC)CC)C>ClCCl>[C:24]([C@H:23]1[O:22][C@H:21]2[C@H:17]([N:18]=[C:19]([N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[S:20]2)[C@@H:16]([O:36][CH2:37][CH:38]=[CH2:39])[C@@H:15]1[O:14][CH2:11][CH:12]=[CH2:13])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86701118HCID 86701118, compound

Product 1

HCID 86701117HCID 86701117, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of DMSO (52 g, 672 mmol) in dichloromethane (500 mL) was treated with oxalyl dichloride (64 g, 505 mmol) at −78° C. for 1 hour, then a solution of 117 (36 g, 84 mmol) in dichloromethane (150 mL) was added. The resulted solution was stirred for 4 hours at −20° C. followed by the addition of triethylamine (85 g, 841 mmol) at −78° C. After stirring at −20° C. for additional 1 hour, the reaction was quenched with water (600 mL), extracted with dichloromethane (2×300 mL). The organic layers combined, washed with brine (2×200 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was purified by silica gel column, eluted with 3% 20% ethyl acetate in petroleum ether to afford 118 (26 g, 73%) as a yellow syrup; [M+H]+ 427.0; 1H NMR (300 MHz, CDCl3) δ 6.02 (d, J=6.3 Hz, 1H), 5.82-5.99 (m, 2H), 5.17-5.35 (m, 4H), 4.20-4.29 (m, 1H), 4.03-4.29 (m, 5H), 3.71-3.77 (m, 2H), 3.25 (s, 3H), 2.14 (s, 3H), 1.52 (s, 9H).

Workup

  1. stirringAfter stirring at −20° C. for additional 1 hour
  2. customthe reaction was quenched with water (600 mL)
  3. extractionextracted with dichloromethane (2×300 mL)
  4. washwashed with brine (2×200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue, which
  8. customwas purified by silica gel column
  9. washeluted with 3% 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c34c53ca636a420b845e200ea9993caf
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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