Dimethyl Sulfoxide → HCID 70159661, compound

HRID 842611Notes

Reaction equation

HRID 842611 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])[CH2:13][N:14]([C@@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])[C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[N+:41]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[O:34][CH2:33][C:12](=[O:11])[CH2:13][N:14]([C@@H:25]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH3:26])[C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:43])=[O:42]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70161058HCID 70161058, compound

Product 1

HCID 70159661HCID 70159661, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (13.0 mL, 150 mmol) in dichloromethane (300 mL) at −78° C. was treated dropwise with DMSO (14.6 mL, 205 mmol), stirred for 10 minutes, treated with the product from Example 1C (46 g, 100 mmol) in dichloromethane (50 mL), stirred for 30 minutes, treated with triethylamine (55 mL, 400 mmol), warmed to 0° C. over 30 minutes, quenched with 10% NaHCO3, and extracted with diethyl ether. The organic layer was washed with 10% NaHSO4, 10% NaHCO3 and brine, dried (Na2SO4) and concentrated. The crude product was filtered through a plug of silica gel with 7:3 hexane/ethyl acetate to provide the title compound. 1H NMR (300 MHz, CDCl3) δ1.52 (d, 3H), 4.00 (d, 1H), 4.22 (d, 1H), 4.30 (d, 0.5H), 4.45 (d, 0.5H), 4.57 (d, 0.5H), 4.71 (d, 0.5H), 5.05-5.30 (m, 2H), 5.51 (q, 0.5H), 5.68 (q, 0.5H), 6.62 (d, 0.5H), 6.92 (d, 0.5H), 7.05 (t, 1H), 7.20-7.42 (m, 10H), 7.50 (t, 1H), 7.88 (d, 1H).

Workup

  1. stirringstirred for 30 minutes
  2. customquenched with 10% NaHCO3
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with 10% NaHSO4, 10% NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. filtrationThe crude product was filtered through a plug of silica gel with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-a69a5c3781f4427dbae2e02cdbd397de
Source dataset
uspto-grants-2002_04
Patent number
US06376488B1

Reaction notes

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