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

HRID 1003865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003865
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1b1a3e2398be4d3290266b1c0588f14b
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046355

Notizen zur Reaktion

Wird geladen…