Methyl iodide → HCID 58573784, compound

HRID 932291Notes

Reaction equation

HRID 932291 reaction equation
[CH:1]([Li])(CC)C.[Cl:6][C:7]1[CH:8]=[C:9]([C@@H:13]2[C@@H:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:17]([C@@H:26]([CH2:35][CH3:36])[CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][S:29]3(=[O:34])=[O:33])[C:16](=[O:37])[C@H:15]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[N:40]=3)[CH2:14]2)[CH:10]=[CH:11][CH:12]=1.IC.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:6][C:7]1[CH:8]=[C:9]([C@@H:13]2[C@@H:18]([C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[N:17]([C@@H:26]([CH2:35][CH3:36])[CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][S:29]3(=[O:34])=[O:33])[C:16](=[O:37])[C@@:15]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[N:40]=3)([CH3:1])[CH2:14]2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 58573946HCID 58573946, compoundHCID 178418400CID 53628100

Product 1

HCID 58573784HCID 58573784, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

sec-Butyllithium (1.4 M in cyclohexane, 0.59 ml, 0.824 mmol) was added to a solution of (3S,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(1,1-dioxidoisothiazolidin-2-yl)butan-2-yl)-3-((6-methoxypyridin-2-yl)methyl)piperidin-2-one (Example 420, Step C, 0.484 g, 0.785 mmol) in THF (3.92 ml) at −78° C. After 15 minutes iodomethane (0.098 ml, 1.57 mmol) was added and the reaction was allowed to warm to room temperature. The reaction contents were poured into saturated sodium bicarbonate (20 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried with sodium sulfate and concentrated in vacuo. Silica gel chromatography (10% step gradient elution 30 to 90% EtOAc in hexanes) afforded the title compound as the first eluting diastereomer.

Workup

  1. customThe reaction contents
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialThe combined organics were dried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. washSilica gel chromatography (10% step gradient elution 30 to 90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-74879d089467480b85b3bc5341250d17
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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