DL-Homoserine → Methyl homoserinate hydrochloride

HRID 910726Notes

Reaction equation

HRID 910726 reaction equation
[NH2:1][CH:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].[CH3:9][Si]([Cl:13])(C)C>CO>[ClH:13].[CH3:9][O:7][C:6](=[O:8])[CH:2]([NH2:1])[CH2:3][CH2:4][OH:5]

Participants

4

Reactant 2

HCID 779DL-HomoserineHCID 6397Chlorotrimethylsilane

Product 1

HCID 53350305Methyl homoserinate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of DL-homoserine (1.00 g, 8.39 mmol) in methanol (40 mL) was placed in an ice bath. Trimethylsilyl chloride (2.34 mL, 18.5 mmol) was added dropwise via syringe. The reaction mixture gradually became homogenous and was further stirred at rt for 14 h, concentrated by rotary evaporation, and further dried under high vacuum. The crude oil thus obtained was used for the next step without further purification. 1H NMR (300 MHz, CD3OD) δ 2.00-2.24 (m, 2H), 3.70-3.80 (m, 2H), 3.85 (s, 3H), 4.12-4.22 (m, 1H). m/z (ESI) 134 [C5H11NO3+H]+.

Workup

  1. customwas placed in an ice bath
  2. concentrationconcentrated by rotary evaporation
  3. customfurther dried under high vacuum
  4. customThe crude oil thus obtained
  5. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-342e9a63bce9417b9949ca747ce99454
Source dataset
uspto-grants-2011_09
Patent number
US08022210B2

Reaction notes

Loading…