Methyl iodide → N-phenyl-N-methylvaline

HRID 1389334Notes

Reaction equation

HRID 1389334 reaction equation
[C:1]1([NH:7][C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[C:17](=O)([O-])[O-].[K+].[K+]>CN(P(N(C)C)(N(C)C)=O)C.O1CCCC1>[C:1]1([N:7]([CH3:17])[C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10867191N-phenylvaline

Product 1

HCID 15383885N-phenyl-N-methylvaline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To the m-phenoxybenzyl ester of N-phenylvaline (0.25 g) in HMPT (1 ml) and tetrahydrofuran (1 ml), at 24°, is added methyl iodide (0.12 ml) followed by potassium carbonate (0.092 g). The reaction mixture is heated at 60° for 4 days. The reaction is worked up by pouring into ice-water (5 ml) and extracting with ether (3×10 ml). The combined ether extracts are washed with water (2×10 ml) and brine (1×5 ml) and dried over calcium sulfate. The product is isolated and purified by preparative TLC to give the m-phenoxybenzyl ester of N-phenyl-N-methylvaline.

Workup

  1. temperatureThe reaction mixture is heated at 60° for 4 days
  2. extractionextracting with ether (3×10 ml)
  3. washThe combined ether extracts are washed with water (2×10 ml) and brine (1×5 ml)
  4. dry with materialdried over calcium sulfate
  5. customThe product is isolated
  6. custompurified by preparative TLC

Sources & evidence

ORD record
ord-33b79e8658c54605bc454913b0fa054b
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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