S-Methyl methanethiosulfonate → Methyldithio-n-methylcysteine

HRID 247805

Reaction equation

HRID 247805 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 87940560Methyldithio-n-methylcysteineYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bd757071dbd74ce7a99d6f4b2f934d57
Source dataset
uspto-grants-1993_05
Patent number
US05208020

Linked notes

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