Dimethyl Sulfoxide → HCID 118207583, compound

HRID 1507253Notes

Reaction equation

HRID 1507253 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:39]=[CH:38][C:15]([CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:27][CH2:26][C@@H:25]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C@H:24]([OH:36])[CH2:23]3)[C:18]2=[O:37])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]1[CH:39]=[CH:38][C:15]([CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:24](=[O:36])[CH2:23]3)[C:18]2=[O:37])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 118207357HCID 118207357, compound

Product 1

HCID 118207583HCID 118207583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of DMSO (0.14 mL, 2 mmol) and DCM (20 mL) at −78° C. under nitrogen was added oxalyl chloride (0.18 mL, 2 mmol) and the reaction mixture was stirred for 10 min. Then 1-(4-fluorobenzyl)-3-(trans-3-hydroxy-4-(4-methoxyphenyl)-piperidin-1-yl)pyrrolidin-2-one (320 mg, 0.8 mmol) was added and the reaction was stirred for one hour at same temperature. Triethylamine (0.56 mL, 4 mmol) was then added, and the reaction mixture was allowed to warm to rt. The mixture was then partitioned between water (100 mL) and DCM (200 mL). The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure to give afford the crude product, which was taken on to step D without further purification. LCMS (method Q) RT 0.68 min (47% AP), m/z 397.1 (M+H+).

Workup

  1. stirringthe reaction was stirred for one hour at same temperature
  2. customThe mixture was then partitioned between water (100 mL) and DCM (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give

Sources & evidence

ORD record
ord-8cd0a185b37240ff923957b4fe1f2e45
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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