Methyl iodide → HCID 58573345, compound

HRID 1048437Notes

Reaction equation

HRID 1048437 reaction equation
[CH2:1]([C@@:4]1([CH3:37])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:34][CH3:35])[C:25]([NH:27][S:28]([CH:31]2[CH2:33][CH2:32]2)(=[O:30])=[O:29])=[O:26])[C:5]1=[O:36])[CH:2]=[CH2:3].[C:38](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH2:1]([C@@:4]1([CH3:37])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:34][CH3:35])[C:25]([N:27]([S:28]([CH:31]2[CH2:33][CH2:32]2)(=[O:30])=[O:29])[CH3:38])=[O:26])[C:5]1=[O:36])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 58573597HCID 58573597, compound

Product 1

HCID 58573345HCID 58573345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)-N-(cyclopropylsulfonyl)butanamide (8 mg, 0.014 mmol; Example 177, Step B) in DMF (1.0 mL) was added potassium carbonate (2.9 mg, 0.021 mmol) and iodomethane (1.1 μL, 0.017 mmol) at rt. The reaction was stirred for 1 hour. After this time more iodomethane (1.1 μL, 0.017 mmol) and potassium carbonate (2.9 mg, 0.021 mmol) was added and the reaction was stirred at rt for 60 hours. After this time the reaction was partitioned between EtOAc (20 mL) and 1.0 M LiCl (5 mL). The separated organic layer was washed with 1.0 M LiCl (5 mL), dried over MgSO4, filtered and evaporated in vacuo to give the title compound.

Workup

  1. stirringthe reaction was stirred at rt for 60 hours
  2. customAfter this time the reaction was partitioned between EtOAc (20 mL) and 1.0 M LiCl (5 mL)
  3. washThe separated organic layer was washed with 1.0 M LiCl (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-83c7958bb53d448299d6767cff6a71f2
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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