Methyl iodide → HCID 54150421, compound

HRID 366221Notes

Reaction equation

HRID 366221 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[H-].[Na+].[C:28](OCC)(=O)C>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]([CH3:28])[C@H:9]([CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 32620192-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoic acid

Product 1

HCID 54150421HCID 54150421, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-tert-Butoxycarbonylamino-3-(1-naphthyl)propionic acid (5.0 g; 0.015 mol) was dissolved in tetrahydrofuran (40 mL). Iodomethane (7.6 mL; 0.12 mol) was added. The reaction mixture was cooled to 0° C. and sodium hydride was added. The reaction mixture was stirred for 48 hours. Ethyl acetate (50 mL) and water (20 mL) were added dropwise. The solvent was removed in vacuo and ether (30 mL) and water (20 mL) were added. The organic phase was washed with an aqueous solution of sodium hydrogen carbonate (pH 8; 30 mL). To the aqueous phases was added citric acid (5%) to pH 3. The aqueous phase was extrated with ethylacetate (3×30 mL). The combined organic phases were washed with water (2×40 mL), an aqueous solution of sodiumthiosulfate (5%; 40 mL) and water (40 mL) and dried (magnesium sulfate). The solvent was removed in vacuo and ether (10 mL) and dicyclohexylamine (8.5 mL) were added. The precipitated crystals were filtered off and dissolved in water (20 mL). Hydrochloric acid was added to pH 2. The reaction mixture was extrated with ethyl acetate (4×40 mL), dried (magnesium sulfate) and evaporated in vacuo to afford 3.97 g of (2R)-2-(tert-butoxycarbonyl methylamino)-3-(1-naphthyl)propionic acid.

Workup

  1. customThe solvent was removed in vacuo and ether (30 mL) and water (20 mL)
  2. additionwere added
  3. washThe organic phase was washed with an aqueous solution of sodium hydrogen carbonate (pH 8; 30 mL)
  4. additionTo the aqueous phases was added citric acid (5%) to pH 3
  5. washThe combined organic phases were washed with water (2×40 mL)
  6. dry with materialan aqueous solution of sodiumthiosulfate (5%; 40 mL) and water (40 mL) and dried (magnesium sulfate)
  7. customThe solvent was removed in vacuo and ether (10 mL) and dicyclohexylamine (8.5 mL)
  8. additionwere added
  9. filtrationThe precipitated crystals were filtered off
  10. dissolutiondissolved in water (20 mL)
  11. additionHydrochloric acid was added to pH 2
  12. dry with materialdried (magnesium sulfate)
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-b6781ace70234a24b3ab0ec4386f906d
Source dataset
uspto-grants-2000_10
Patent number
US06127391

Reaction notes

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