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

HRID 1585331Notes

Reaction equation

HRID 1585331 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C@H:7]([C:11]([OH:13])=[O:12])[CH:8]([CH3:10])[CH3:9]>[OH-].[Na+].O1CCOCC1>[CH3:5][O:4][C:2]([NH:6][C@H:7]([C:11]([OH:13])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:3]

Participants

5

Reactant 2

HCID 6287L-ValineHCID 6586Methyl chloroformate

Product 1

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

5.67 g (60 mmol) of methyl chloroformate (Fluka, Buchs, Switzerland) are added to 7.0 g (60 mmol) of L-valine in 100 ml of 2N NaOH and 30 ml of dioxane (→exothermic reaction), and this mixture is subsequently stirred at RT for 18 h. The reaction mixture is extracted with methylene chloride, and the aqueous phase is acidified with 27 ml of 4N HCl and once again extracted with methylene chloride. Drying and evaporating the latter methylene chloride phase affords the title compound: tRet (I)=7.2 min; 1H-NMR (200 MHz, CD3OD): 0.96 (t, J=7 Hz, 6H), 2.16 (m, 1H), 3.67 (s, 3H), 4.06 (m, 1H), 7.07 (d, J=8 Hz, HNpartially exchanged).

Workup

  1. extractionThe reaction mixture is extracted with methylene chloride
  2. extractiononce again extracted with methylene chloride
  3. customDrying
  4. customevaporating the latter methylene chloride phase

Sources & evidence

ORD record
ord-b898467eacdc416f91627c80f9adcaf4
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

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