Methyl iodide → HCID 178463214, compound

HRID 1469157Notes

Reaction equation

HRID 1469157 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:32]I>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:17][CH2:18][C@H:19]([N:22]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH3:32])[CH2:20][CH2:21]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178463215HCID 178463215, compound

Product 1

HCID 178463214HCID 178463214, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (3 g, 6.41 mmol, see, e.g., WO2012142504) in THF (30 mL), NaH (0.184 g, 7.69 mmol) was added at 0° C. and stirred it at same temperature for 20 min. Then methyl iodide (9.10 g, 64.10 mmol) was added at 0° C. and reaction was stirred for overnight at room temperature. On completion, reaction was quenched with ice water and extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the crude title compound that was used without further purification (3 g, 97.4% yield).

Workup

  1. customreaction
  2. stirringwas stirred for overnight at room temperature
  3. customOn completion, reaction
  4. customwas quenched with ice water
  5. extractionextracted with dichloromethane
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-133d22cad3ac4e9baad725a2d6d1aaf3
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

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