Ethanol → Alanine, 2-methyl-, ethyl ester

HRID 1066190Notes

Reaction equation

HRID 1066190 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].[CH2:8](O)[CH3:9]>>[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([O:5][CH2:8][CH3:9])=[O:4]

Participants

3

Reactant 2

HCID 702EthanolHCID 6119Aminoisobutyric acid

Product 1

HCID 70683Alanine, 2-methyl-, ethyl esterYield 99%

Procedure

A solution of 2-aminoisobutyric acid (3.3 g, 32 mmol) in absolute ethanol (100 mL) was cooled to −78° C. and HCl(g) bubbled in for 10 minutes. The flask was sealed with a septum and stirred at ambient temperature. After 14 hours the mixture was concentrated in vacuo to afford 5.3 g (99% yield) of ethyl 2-aminoisobutyrate as a white solid; NMR (CDCl3) 8.9 (br s, 3), 4.1 (q, 2), 1.7 (s, 6), 1.3 (t, 3) ppm.

Workup

  1. customHCl(g) bubbled in for 10 minutes
  2. customThe flask was sealed with a septum
  3. concentrationAfter 14 hours the mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2ecfcf1539fc4aed80c138a53997c200
Source dataset
uspto-grants-2001_06
Patent number
US06242454B1

Reaction notes

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