Water → HCID 86609795, compound

HRID 1725330Notes

Reaction equation

HRID 1725330 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[O:12].O>[OH-].[Na+]>[CH3:17][O:16][CH2:15][CH2:14][O:13][C:11]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6106L-LeucineHCID 694002-Methoxyethyl chloroformate

Product 1

HCID 86609795HCID 86609795, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of L-leucine (25 g, 0.19 mol) was dissolved in 2M NaOH (0.12 L) was slowly added 2-methoxyethyl chloroformate (30 g, 0.22 mol) and 1M NaOH at the same time under the ice-cooled condition. The mixture was stirred at room temperature for 18 hours, diluted into water (600 mL) and washed with ethyl ether (2×200 mL). The aqueous phase was cooled in an ice bath and acidified to pH 3 with 6M HCl. This mixture was extracted with ethyl acetate (EtOAc) (5×150 mL). The organic phase was dried over anhydrous MgSO4 and filtered, and the filtrate was concentrated in vacuo to yield N-((2-methoxyethoxy)carbonyl)-L-leucine (41 g, 92%) as a colorless oil.

Workup

  1. temperaturecooled condition
  2. washwashed with ethyl ether (2×200 mL)
  3. temperatureThe aqueous phase was cooled in an ice bath
  4. extractionThis mixture was extracted with ethyl acetate (EtOAc) (5×150 mL)
  5. dry with materialThe organic phase was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-90027de2cb6e4f12a87046639e61cedc
Source dataset
uspto-grants-2009_02
Patent number
US07491705B2

Reaction notes

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