Methanol → Methyl(2-hydroxybutylamino)acetate Hydrochloride

HRID 480588Notes

Reaction equation

HRID 480588 reaction equation
[OH:1][CH:2]([CH2:9][CH3:10])[CH2:3][NH:4][CH2:5][C:6]([OH:8])=[O:7].S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[CH3:15][O:7][C:6](=[O:8])[CH2:5][NH:4][CH2:3][CH:2]([OH:1])[CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 18765545(2-Hydroxybutylamino)acetic acid

Product 1

HCID 18765569Methyl(2-hydroxybutylamino)acetate Hydrochloride

Procedure

2.85 g of (2-hydroxybutylamino)acetic acid in 100 ml of methanol are cooled in an ice-acetone cooling bath, then 7.27 ml of thionyl chloride is added dropwise within 20 minutes. The reaction mixture is left overnight to come back to ambient temperature and then evaporated to dryness. Methanol is added several times to the residue and this is then concentrated by evaporation. The crude product is reacted further without any more purification. Yield: 3.83 g (100% of theory); Rf value: 0.85 (reversed phase ready-made TLC plate (E. Merck), methanol/5% sodium chloride solution=6:4); mass spectrum (ESI+): m/z=162 [M+H]+.

Workup

  1. customto come back to ambient temperature
  2. customevaporated to dryness
  3. additionMethanol is added several times to the residue
  4. concentrationthis is then concentrated by evaporation
  5. customThe crude product is reacted further without any more purification

Sources & evidence

ORD record
ord-d29135f0633b41838c4d59dea7f4f488
Source dataset
uspto-grants-2003_11
Patent number
US06653305B2

Reaction notes

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