DL-Homoserine → Methyl homoserinate hydrochloride

HRID 1678287

Reaktionsgleichung

Reaktionsgleichung von HRID 1678287
[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]

Komponenten

4

Edukt 2

HCID 779DL-HomoserineHCID 6397Chlorotrimethylsilane

Produkt 1

HCID 53350305Methyl homoserinate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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 (EST) 134 [C5H11NO3+H]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-14d8fee5246d49f8bafe8696fa98ee74
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008494B2

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