Methyl iodide → HCID 86718365, compound

HRID 1518758Notes

Reaction equation

HRID 1518758 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:25])[CH:7]=[CH:8][C@@H:9]([CH3:24])[C@H:10]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)[CH3:4].[CH3:26]I.OS([O-])(=O)=O.[Na+]>C1COCC1.CN(C=O)C.CCOCC>[CH2:3]([O:5][C:6](=[O:25])[CH:7]=[CH:8][C@@H:9]([CH3:24])[C@H:10]([N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:26])[C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)[CH3:4]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 86718364HCID 86718364, compound

Product 1

HCID 86718365HCID 86718365, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of NaH (0.707 g, 17.7 mmol) in THF (10.7 mL) at 0° C. was added 2.12b (1.14 g, 3.53 mmol) in DMF (1 mL), followed by MeI (1.33 mL, 21.2 mmol). After stirring at 0° C. for 1 hour, the reaction mixture was poured onto a ice cold mixture of 1.0 M aq. NaHSO4 solution and Et2O. The separated organic layer was washed with brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (0-50% EtOAc/heptane) to give 2.12c (1.08 g, 91% yield). MS m/z (M+23) 360.1

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (0-50% EtOAc/heptane)

Sources & evidence

ORD record
ord-26972f0161814498ab314ab87ce559d3
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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