Methyl iodide → HCID 178493931, compound

HRID 1023264Notes

Reaction equation

HRID 1023264 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C@H:18]4[CH2:23][CH2:22][C@H:21]([NH:24][C:25]([C:27]5([OH:30])[CH2:29][CH2:28]5)=[O:26])[CH2:20][CH2:19]4)[CH2:12][CH2:11]3)[C:4]=2[O:3][CH2:2]1.[H-].[Na+].[CH3:33]I>C1COCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C@H:18]4[CH2:23][CH2:22][C@H:21]([NH:24][C:25]([C:27]5([O:30][CH3:33])[CH2:29][CH2:28]5)=[O:26])[CH2:20][CH2:19]4)[CH2:14][CH2:15]3)[C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178523684HCID 178523684, compound

Product 1

HCID 178493931HCID 178493931, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To trans-1-Hydroxy-cyclopropanecarboxylic acid {4-[2-(4-benzo[1,3]dioxol-4-yl-piperazin-1-yl)-ethyl]-cyclohexyl}-amide (20 mg, 48.1 μmol, Eq: 1.00) in THF (500 μl) was added NaH (3.37 mg, 84.2 μmol, Eq: 1.75) and methyl iodide (17.1 mg, 7.52 μl, 120 μmol, Eq: 2.5). After 2 hours the reaction mixture was diluted with water (300 ul). The crude reaction mixture was concentrated in vacuo. The residue was suspended with 5 mL sat NaHCO3 and extracted with dichloromethane (2×10 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 0% to 15% MeOH in dichloromethane) to yield the title compound as an off-white solid (12.1 mg, 58.5%), MS (ISP) m/z=430.2 [(M+H)+].

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. extractionextracted with dichloromethane (2×10 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 10 g, 0% to 15% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-7e8650d2074a4571a7245cb0520e0e92
Source dataset
uspto-grants-2014_05
Patent number
US08722683B2

Reaction notes

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