Dimethyl Sulfoxide → HCID 86701120, compound

HRID 1396282Notes

Reaction equation

HRID 1396282 reaction equation
CS(C)=O.[CH2:5]([N:7]([C:15]1[S:27][C@@H:26]2[C@@H:17]([C@@H:18]3[C@@H:23]([C@@H:24]([CH2:28][OH:29])[O:25]2)[O:22][C:21]([O:31][CH3:32])([CH3:30])[C:20]([O:34][CH3:35])([CH3:33])[O:19]3)[N:16]=1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].C(N(CC)CC)C>ClCCl>[CH2:5]([N:7]([C:15]1[S:27][C@@H:26]2[C@@H:17]([C@@H:18]3[C@@H:23]([C@@H:24]([CH:28]=[O:29])[O:25]2)[O:22][C:21]([O:31][CH3:32])([CH3:30])[C:20]([O:34][CH3:35])([CH3:33])[O:19]3)[N:16]=1)[C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH3:6]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 69280815HCID 69280815, compound

Product 1

HCID 86701120HCID 86701120, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of DMSO (40 g, 0.52 mol) in anhydrous dichloromethane (1.5 L) was treated with oxallyl dichloride (49 g, 0.39 mol) at −78° C. for 1 hour, followed by addition of 123 (30 g, 65 mmol). The resulting solution was stirred for 4 hours at −30° C. and then cooled down to −78° C. again at which time triethylamine (86 g, 0.85 mol) was added. After 1 hour at −50° C., the reaction mixture was quenched by H2O (500 mL), washed with brine (3×100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a short silica gel column, eluted with 30% ethyl acetate in petroleum ether to give 124 as a brown syrup (18 g, 60%). (ES, m/z) [M+H]+ 461.0; 1H NMR (300 MHz, CDCl3) δ 8.93 (s, 1H), 8.90 (s, 1H), 6.15-6.18 (m, 2H), 4.41-4.45 (m, 1H), 4.28-4.30 (m, 1H), 3.76-4.09 (m, 13H), 3.38 (s, 3H), 3.32 (s, 3H), 3.28 (s, 3H), 3.26 (s, 3H), 1.58 (s, 9H), 1.47 (s, 3H), 1.43 (s, 3H), 1.39 (s, 3H), 1.37 (s, 3H), 1.14-1.21 (m, 6H).

Workup

  1. additionwas added
  2. waitAfter 1 hour at −50° C.
  3. customthe reaction mixture was quenched by H2O (500 mL)
  4. washwashed with brine (3×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto give a residue, which
  8. customwas purified by a short silica gel column
  9. washeluted with 30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d8c397e11b0f442d9fcbc6a555cd02d4
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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