D-1,4-Dithiothreitol → Dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester

HRID 356510Notes

Reaction equation

HRID 356510 reaction equation
[C:1]([C:5]1[C:6]([S:19]C#N)=[CH:7][C:8]([CH3:18])=[C:9]([O:11][S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].SC[C@H]([C@@H](CS)O)O.OP([O-])(O)=O.[K+]>CCO>[C:1]([C:5]1[C:6]([SH:19])=[CH:7][C:8]([CH3:18])=[C:9]([O:11][S:12](=[O:16])(=[O:17])[N:13]([CH3:14])[CH3:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 446094D-1,4-DithiothreitolHCID 516951Monobasic potassium phosphateHCID 10496539Dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester

Product 1

HCID 10662229Dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stirrer and condenser were added 1.1 g (3.3 mmol) of dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester (prepared in Example SSS), dithiothreitol (1.29 g, 8.35 mmol), EtOH (40 mL), and 0.02M KH2PO4 buffer solution (5 mL), respectively. The reaction was refluxed overnight. The mixture was then quenched with H2O (250 mL) and extracted with a 1:1 mixture of hexanes:Et2O. The organic layer was again washed with H2O and brine, dried (MgSO4) and concentrated. The residue was dried under high vacuum to yield the title compound. 1H NMR (CDCl3) δ 1.45 (s, 9 H), 2.25 (s, 3 H), 3.02 (s, 6 H), 3.57 (s, 1 H), 7.01 (s, 1 H), 7.28 (s, 1 H).

Workup

  1. customTo a round bottom flask equipped with a magnetic stirrer and condenser
  2. temperatureThe reaction was refluxed overnight
  3. customThe mixture was then quenched with H2O (250 mL)
  4. extractionextracted with a 1:1 mixture of hexanes
  5. washThe organic layer was again washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-0fc603a7f9a749d28b0d169bb4db6176
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

Loading…