Methanol → Methyl 2-aminoisobutyrate hydrochloride

HRID 1177999Notes

Reaction equation

HRID 1177999 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].S(Cl)([Cl:10])=O.[CH3:12]O>>[ClH:10].[CH3:12][O:4][C:3](=[O:5])[C:2]([NH2:1])([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 6119Aminoisobutyric acidHCID 24386Thionyl Chloride

Product 1

HCID 13258034Methyl 2-aminoisobutyrate hydrochlorideYield 96.62%

Procedure

To a stirred solution of 2-amino-2-methyl-propionic acid (1 gm, 9.6 mol) in MeOH (20 ml) cooled in ice bath, thionylchloride (1.38 gm, 0.85 ml, 11.63 mol) was added drop wise slowly and left at room temperature overnight. The reaction mass was concentrated to get the residue which was washed with hexane twice to afford 2-amino-2-methyl-propionic acid methyl ester hydrochloride salt 1.43 gm (96.62%). 1H NMR (DMSO-d6): δ 8.9 (s, 2H), 8.6 (s, 1H), 3.8 (s, 3H), 1.55 (s, 6H), 1.5 (s, 3H).

Workup

  1. concentrationThe reaction mass was concentrated
  2. customto get the residue which
  3. washwas washed with hexane twice

Sources & evidence

ORD record
ord-cf3080b5c4cf46c9bf4cda31f7677424
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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