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

HRID 1003865Notes

Reaction equation

HRID 1003865 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 0.02 M 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-1b1a3e2398be4d3290266b1c0588f14b
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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