L-Alanine → 2-Methylpropyl (2S)-2-aminopropanoate hydrochloride

HRID 23060

Reaction equation

HRID 23060 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].S(Cl)([Cl:9])=O.[CH2:11](O)[CH:12]([CH3:14])[CH3:13]>>[ClH:9].[CH2:11]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH2:1])[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 5950L-AlanineHCID 6560IsobutanolHCID 24386Thionyl Chloride

Product 1

HCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Procedure

A mixture of 35.64 g (0.4 mol) of (D,L)-alanine (Aldrich) (or L-alanine (Aldrich)); 44 mL (0.6 mol) of thionyl chloride (Aldrich) and 200 mL of isobutanol was refluxed for 1.5 hours and the volatiles were removed completely on a rotavapor of 90° C. under reduced pressure to give (D,L)-alanine iso-butyl ester hydrochloride (or L-alanine iso-butyl ester hydrochloride), which was pure enough to be used for further transformations.

Workup

  1. customthe volatiles were removed completely on a rotavapor of 90° C. under reduced pressure

Sources & evidence

ORD record
ord-67ada832f8c24662847c20f8da7631de
Source dataset
uspto-grants-2005_02
Patent number
US06849650B2

Linked notes

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