S-Methyl methanethiosulfonate → Methyldithio-n-methylcysteine

HRID 247805

Reaktionsgleichung

Reaktionsgleichung von HRID 247805
[CH3:1][NH:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].[CH3:9][S:10][S:11](C)(=O)=O>O.C(O)C>[CH3:9][S:10][S:11][N:2]([CH3:1])[C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5]

Komponenten

5

Edukt 2

HCID 18064S-Methyl methanethiosulfonateHCID 452303N-Methyl-L-cysteine

Produkt 1

HCID 87940560Methyldithio-n-methylcysteineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of N-methylcysteine (Undhein, K., & Eidem, A., 23 Acta Chem. Scandinavica 3129-3133 (1970) (1.5 g, 11.1 mmol) in H2O (20 ml) was stirred at room temperature, under an atmosphere of argon, and treated with a solution of methyl methanethiol sulfonate (3.0 ml, 29.2 mmol) in ethanol (10 ml). The reaction mixture was stirred at this temperature for two hours and then diluted with H2O (100 ml) and washed with ether (4×40 ml). The aqueous layer was acidified to pH 2 and passed through an Amberlite IRA 93 (--OH form) column. The column was washed with water and the effluent was collected and evaporated to dryness under reduced pressure to give a white solid (1.2g, 60%), mp 194°-5° C. NMR (D2O, TMS ext. standard): δ2.2(3H, s), 2.5(3H, s), 3.2(2H,d), 3.7(1H,q).

Aufarbeitung

  1. washwashed with ether (4×40 ml)
  2. washThe column was washed with water
  3. customthe effluent was collected
  4. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd757071dbd74ce7a99d6f4b2f934d57
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208020

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