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

HRID 1377160Notes

Reaction equation

HRID 1377160 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-072d30d0a9044728abc2604fa0763a3e
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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