Methyl iodide → HCID 69352940, compound

HRID 1277294Notes

Reaction equation

HRID 1277294 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:20](OCC)(=O)C.[OH-].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9]([CH:11]([CH3:20])[CH2:12][CH:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 95441Poly-gamma-benzyl L-glutamate

Product 1

HCID 69352940HCID 69352940, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In THF (500 ml) was dissolved 4-[(benzyloxy) carbonyl]-aminobutyric acid (25.0 g) , and to the mixture was gradually added at -5° C. methyl iodide (37.4 g). Under nitrogen atmosphere, the mixture was stirred at 0° C. for 15 minutes and then at room temperature for 24 hours. To the mixture was added ethyl acetate (300 ml) and then water (800 ml). The mixture was made pH 11 with sodium hydroxide and washed with ether (400 ml×2). The aqueous layer was made pH 2 with concentrated hydrochloric acid and extracted with ethyl acetate (1000 ml and 500 ml×3). The organic layer was washed with 1M sodium thiosulf ate solution (300 ml) and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give 4-[(benzyloxy)carbonyl]-4-methyl-aminobutyric acid (26.3 g).

Workup

  1. waitat room temperature for 24 hours
  2. washwashed with ether (400 ml×2)
  3. extractionextracted with ethyl acetate (1000 ml and 500 ml×3)
  4. washThe organic layer was washed with 1M sodium thiosulf ate solution (300 ml)
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c3771a78852042f3a463839f77c3e2a4
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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