L-Valine → (2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

HRID 643066Notes

Reaction equation

HRID 643066 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].Cl[C:12]([O:14][CH3:15])=[O:13]>O1CCOCC1>[CH3:15][O:14][C:12]([NH:1][C@@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])=[O:13]

Participants

5

Reactant 3

HCID 6287L-ValineHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (L)-Valine (7.43 g, 57 mmol) in dioxane (28 mL) was treated with 2N sodium hydroxide (93.5 mL, 3.3 equivalents) and methyl chloroformate (8.75 mL, 2 equivalents), stirred at 60° C. for 16 hrs and cooled to room temperature. The mixture was extracted with dichloromethane (2×). The mixture was acidified with 4N HCl, and extracted with ethyl acetate (3×), dried over sodium sulfate, filtered and the solvents were evaporated to give 8.6 g (80%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with dichloromethane (2×)
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvents were evaporated

Sources & evidence

ORD record
ord-bdb988beab664fe4b5a841f33f531ded
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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