Dimethylformamide → HCID 58573313, compound

HRID 931989Notes

Reaction equation

HRID 931989 reaction equation
[CH3:1][S-:2].[Na+].CC1C=CC(S(O[CH2:15][C:16]2(C)[CH2:21][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C@@H:19]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:18]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=3[O:45][CH3:46])[C:17]2=[O:47])(=O)=O)=CC=1.[CH3:49]N(C=O)C>O>[Cl:28][C:24]1[CH:23]=[C:22]([C@@H:20]2[C@@H:19]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[N:18]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=3[O:45][CH3:46])[C:17](=[O:47])[C@@:16]([CH3:15])([CH2:1][S:2][CH3:49])[CH2:21]2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 58573562HCID 58573562, compound

Product 1

HCID 58573313HCID 58573313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium thiomethoxide (0.193 g, 2.76 mmol) was added to a solution of ((5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxopiperidin-3-yl)methyl 4-methylbenzenesulfonate (Example 88, Step C) (0.738 g, 1.104 mmol) in anhydrous DMF (5.52 mL) at rt under nitrogen. The reaction mixture was heated at 50° C. for 8 hours before being cooled to rt, diluted with water and extracted with ether three times. The organics were pooled, washed with water three times, sat. aq. NaCl solution, dried (MgSO4), filtered and concentrated in vacuo to provide a colorless oil. Purification using a 40 g SiO2 column and eluting with 15 to 40% EtOAc/hexanes provided the title compound as a colorless foam.

Workup

  1. temperaturebefore being cooled to rt
  2. extractionextracted with ether three times
  3. washwashed with water three times, sat. aq. NaCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a colorless oil
  8. customPurification
  9. washeluting with 15 to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-101889838463414bb517cb65e0ccef86
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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