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

HRID 1291774Notes

Reaction equation

HRID 1291774 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].[NH2:6][C@H:7]([C:11]([OH:13])=[O:12])[CH:8]([CH3:10])[CH3:9]>[OH-].[Na+].O1CCOCC1>[CH3:1][O:2][C:3]([NH:6][C@H:7]([C:11]([OH:13])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:4]

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 chloroformic acid methyl ester 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 the mixture is then stirred for 18 h at RT. The reaction mixture is extracted with methylene chloride and the aqueous phase is acidified with 27 ml of 4N HCl and extracted again with methylene chloride. Drying and concentration by evaporation of the latter methylene chloride phase yields 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. extractionextracted again with methylene chloride
  3. customDrying
  4. concentrationconcentration
  5. customby evaporation of the latter methylene chloride phase

Sources & evidence

ORD record
ord-0c36d4450bd2442ebc08b02c6f1d8985
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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