Methyl iodide → N-methyl-N-6-bromohexanoyl-L-leucine ethyl ester

HRID 864467Notes

Reaction equation

HRID 864467 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:21])[C@H:7]([CH2:17][CH:18]([CH3:20])[CH3:19])[NH:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH3:4].[CH3:22]I>C1COCC1>[CH2:3]([O:5][C:6](=[O:21])[C@H:7]([CH2:17][CH:18]([CH3:20])[CH3:19])[N:8]([CH3:22])[C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22866411N-6-bromohexanoyl-L-leucine ethyl ester

Product 1

HCID 22866412N-methyl-N-6-bromohexanoyl-L-leucine ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil; 2.0 g, 50 mmol) was added to a stirred solution of N-6-bromohexanoyl-L-leucine ethyl ester (15.0 g, 45 mmol) in anhydrous THF (150 ml) at 0° C. After the effervesence had ceased methyl iodide (8.4 ml) was added. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate, washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated to give crude N-methyl-N-6-bromohexanoyl-L-leucine ethyl ester (14.0 g, 89%) as a pale yellow oil which was used directly in the next step.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3639f26501d4ed28d8a2c71019678fb
Source dataset
uspto-grants-1996_10
Patent number
US05563151

Reaction notes

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