Water → HCID 86609795, compound

HRID 2206346Notes

Reaction equation

HRID 2206346 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15](Cl)=[O:16].O>[OH-].[Na+]>[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:16]

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

L-Leucine (25 g, 0.19 mol) was dissolved in a 2M aqueous sodium hydroxide solution (0.12 L), to which chloroformic acid 2-methoxyethyl ester (30 g, 0.22 mol) and a 1M aqueous sodium hydroxide solution were simultaneously and slowly added under ice-cold conditions. This solution was stirred at room temperature for 18 hours, followed by dilution with water (600 mL) and washing with diethyl ether (2×200 mL). The aqueous layer was cooled in an ice bath, and the pH was adjusted to 3 with 6M hydrochloric acid. This solution was extracted with ethyl acetate (5×150 mL). The organic layer was dehydrated with anhydrous magnesium sulfate and concentrated in vacuo to yield N-((2-methoxyethoxy)carbonyl)-L-leucine (41 g, 92%) as a colorless oil.

Workup

  1. additionslowly added under ice-cold conditions
  2. washwashing with diethyl ether (2×200 mL)
  3. temperatureThe aqueous layer was cooled in an ice bath
  4. extractionThis solution was extracted with ethyl acetate (5×150 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b8bc0dfead246ad8320bee3b197053a
Source dataset
uspto-grants-2016_06
Patent number
US09371359B2

Reaction notes

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