Ethanol → Alanine, 2-methyl-, ethyl ester

HRID 450034

Reaction equation

HRID 450034 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH2:12](O)[CH3:13]>>[CH2:12]([O:4][C:3](=[O:5])[C:2]([NH2:1])([CH3:7])[CH3:6])[CH3:13]

Participants

4

Conditions

Temperature
0 °C

Procedure

2-Amino-2-methyl-propionic acid (1.0 g, 9.69 mmol) was dissolved in ethanol (15 ml) and cooled to 0° C. Thionyl chloride (1.7 g, 14.53 mmol, 1.5 eq) was added to the reaction mixture, which was then heated to reflux overnight. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was concentrated and dried to give 2-amino-2-methyl-propionic acid ethyl ester (0.8 g, 63%). The crude compound was used in the next stage without purification.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water and ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customdried

Sources & evidence

ORD record
ord-b9501f6ba7be4d5b99e63345d16d1dfc
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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