Dimethyl Sulfoxide → HCID 71135270, compound

HRID 1468839Notes

Reaction equation

HRID 1468839 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([CH:14]([OH:42])[C:15]2[C:39]([F:40])=[CH:38][C:18]([CH2:19][O:20][CH2:21][C@@H:22]3[CH2:24][C@@H:23]3[CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:17][C:16]=2[F:41])[CH2:13][CH2:12]1.CCN(CC)CC>C(Cl)Cl>[CH:11]1([C:14]([C:15]2[C:16]([F:41])=[CH:17][C:18]([CH2:19][O:20][CH2:21][C@@H:22]3[CH2:24][C@@H:23]3[CH:25]3[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]3)=[CH:38][C:39]=2[F:40])=[O:42])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86717790HCID 86717790, compound

Product 1

HCID 71135270HCID 71135270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (0.09 mL of a 2M soln in DCM, 0.177 mmol) was dissolved in DCM (0.8 mL) at −78° C. DMSO (35 mg, 0.44 mmol) was added, and the resulting solution was stirred at −78° C. for 5 minutes. A solution of the product from step A (40 mg, 0.09 mmol) in DCM (1 mL) was added followed by Et3N (90 mg, 0.89 mmol). The reaction was warmed to room temperature, and stirred at that temperature for 15 minutes. The reaction was quenched with sat. NH4Cl(aq.), and extracted with DCM. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (0-15% EtOAc in hexanes) which provided title compound. 1H NMR (500 MHz, CDCl3) δ 6.94 (dd, 2H), 4.58 (d, 1H), 4.49 (d, 1H), 4.18-4.00 (br m, 2H), 3.58-3.46 (m, 2H), 2.74-2.61 (m, 2H), 1.83 (d, 1H), 1.73 (d, 1H), 1.47 (s, 9H), 1.38-1.19 (m, 5H), 1.13-1.09 (m, 2H), 0.97-0.88 (m, 1H), 0.80-0.68 (m, 2H), 0.06-0.00 (m, 1H). MS (ESI) m/z 450 [M+H]+.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred at that temperature for 15 minutes
  3. customThe reaction was quenched with sat. NH4Cl(aq.)
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via silica gel column chromatography (0-15% EtOAc in hexanes) which

Sources & evidence

ORD record
ord-ca4deea1061542b9aa15296678862e37
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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