Bromoacetonitrile → (R)-2-Amino-3-((cyanomethyl)thio)propanoic acid

HRID 264008

Reaktionsgleichung

Reaktionsgleichung von HRID 264008
O.Cl.[NH2:3][C@H:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].[OH-].[Na+].Br[CH2:13][C:14]#[N:15]>O1CCOCC1>[C:14]([CH2:13][S:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[NH2:3])#[N:15]

Komponenten

5

Edukt 3

HCID 11534BromoacetonitrileHCID 14798Sodium HydroxideHCID 23462L-Cysteine hydrochloride monohydrate

Produkt 1

HCID 36688841(R)-2-Amino-3-((cyanomethyl)thio)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A 360 mL aqueous solution of commercially available (Aldrich) L-cysteine hydrochloride monohydrate (60.0 g, 341.7 mmole) and sodium hydroxide (27.33 g, 683.4 mmole), at room temperature, is treated with a solution of bromoacetonitrile (44.5 g, 370.6 mmole) in 130 mL of dioxane over 30 minutes. The reaction is stirred for 18 hours, during which time a thick precipitate will form. The solid is filtered off, washed with diethyl ether (100 mL) and dried under high vacuum at 40° C. to give the title compound.

Aufarbeitung

  1. customwill form
  2. filtrationThe solid is filtered off
  3. washwashed with diethyl ether (100 mL)
  4. customdried under high vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-449181e19a584136877ea9844e134996
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646165

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