L-Valine → N-(Methoxycarbonyl)-D-valine

HRID 1615100Notes

Reaction equation

HRID 1615100 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C([O-])(O)=O.[Na+].[CH3:14][O:15][C:16](Cl)=[O:17]>O>[CH3:14][O:15][C:16]([NH:1][C@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])=[O:17]

Participants

5

Reactant 3

HCID 6287L-ValineHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 28377962N-(Methoxycarbonyl)-D-valineYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a mixture of L-valine (220 mg, 1.9 mmol) and NaHCO3 (482 mg, 5.6 mmol) in H2O (6 mL) at 0° C. is added dropwise methylchloroformate (0.25 mL, 3.25 mmol). The reaction mixture is stirred for 2 hours at 0-5° C. The mixture is diluted with water and washed with Et2O. The aqueous layer is acidified with 1N HCl to pH 3 and the product is extracted with EtOAc. The combined organic layers are washed with brine, dried over sodium sulfate and concentrated in vacuum. The residue is triturated with hexanes-Et2O to give (R)-2-methoxycarbonylamino-3-methyl-butyric acid (248 mg, 75%).

Workup

  1. washwashed with Et2O
  2. extractionthe product is extracted with EtOAc
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuum
  6. customThe residue is triturated with hexanes-Et2O

Sources & evidence

ORD record
ord-41cd4d163ca747de9e52f1e632976e86
Source dataset
uspto-grants-2014_07
Patent number
US08765731B2

Reaction notes

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