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

HRID 1625518Notes

Reaction equation

HRID 1625518 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:18]([O:20][CH3:21])=[O:19]>>[CH3:21][O:20][C:18]([NH:1][C@@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])=[O:19]

Participants

5

Reactant 4

HCID 6287L-ValineHCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidYield 67%

Procedure

L-Valine (140 g, 1.195 mol) is added to a stirred solution of 1 M sodium hydroxide (1.183 L, 1.183 mol). After complete dissolution, sodium carbonate (65.8 g, 621.4 mmol) is added followed by methyl chloroformate (122 g, 99.75 mL, 1.291 mol) at 0° C. over 40 minutes. The reaction mixture is stirred at rt for 3.5 hours, then washed with diethyl ether (3×200 ml). The aqueous layer is cooled to 0° C., and acidified to pH 1-2. The white solid formed is filtered on a Buchner, washed with cold water and dried to afford the title compound (2S)-2-(methoxycarbonylamino)-3-methyl-butanoic acid (140 g, 67%).

Workup

  1. additionis added
  2. washwashed with diethyl ether (3×200 ml)
  3. temperatureThe aqueous layer is cooled to 0° C.
  4. customThe white solid formed
  5. filtrationis filtered on a Buchner
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-3e175542788d4453b3a71abba0947c8f
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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