Acetyl chloride → L-Serine, ethyl ester, hydrochloride (1:1)

HRID 507710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507710
[NH2:1][C@@H:2]([CH2:6][OH:7])[C:3]([O-:5])=[O:4].[C:8]([Cl:11])(=O)[CH3:9]>C(O)C>[ClH:11].[NH2:1][C@@H:2]([CH2:6][OH:7])[C:3]([O:5][CH2:8][CH3:9])=[O:4]

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 5460791(2S)-2-amino-3-hydroxypropanoate

Produkt 1

HCID 2724185L-Serine, ethyl ester, hydrochloride (1:1)Ausbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (2S)-2-amino-3-hydroxypropanoate (25 g, 238 mmol) and acetyl chloride (34 ml, 476 mmol) in absolute ethanol (250 ml) was stirred at 50° for 18 hr. The volatiles were removed in vacuo until the volume was reduced to ˜100 ml. Upon cooling the resultant precipitate was collected, washed with ether and hexane to give the title compound as a white powder (26.3 g, 65%). δH NMR (DMSO d6) 8.47 (3H, br s), 5.58 (1H, dd), 4.20 (2H, q), 4.08 (1H, t), 3.81 (2H, dd), 1.23 (3H, t).

Aufarbeitung

  1. customThe volatiles were removed in vacuo until the volume
  2. temperatureUpon cooling the resultant precipitate
  3. customwas collected
  4. washwashed with ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-94e47875897a4b89b6edce9a3e00626d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786177B2

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