D-1,4-Dithiothreitol → HCID 10786892, compound

HRID 1003873Notes

Reaction equation

HRID 1003873 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]([C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([S:26]C#N)=[CH:18][C:17]=1[CH3:29])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])[CH3:3].SC[C@H]([C@@H](CS)O)O.OP([O-])(O)=O.[K+]>CCO>[CH3:15][C:12]([O:11][C:9]([N:8]([C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([SH:26])=[CH:18][C:17]=1[CH3:29])[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:10])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 446094D-1,4-DithiothreitolHCID 516951Monobasic potassium phosphateHCID 53864568HCID 53864568, compound

Product 1

HCID 10786892HCID 10786892, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [4-(cyanothio)-5-(1,1-dimethylethyl)-2-methylphenyl]-imidodicarbonic acid bis(1,1-dimethylethyl) ester obtained in Example EEEE (11.65 g, 27.7 mmol) in denatured EtOH (160 mL) was added dithiothreitol (16.8 g, 109.1 mmol), and 0.2 M KH2PO4 solution (40 mL). The mixture was stirred overnight at 50° C. The solvent was evaporated, and H2O and CHCl3 were added; the organic layer was washed with brine, dried (Na2SO4) filtered and concentrated. The resulting residue was flash chromatographed on silica gel, eluting with 1:1 CHCl3 :hexanes switching to 19:1 CHCl3 :EtOAc, to afford the title compound. 1H NMR (CDCl3) δ 1.40-1.46 (m, 27 H), 2.07 (s, 3 H), 7.00 (s, 1 H), 7.05 (s, 1 H).

Workup

  1. customThe solvent was evaporated
  2. additionH2O and CHCl3 were added
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel
  8. washeluting with 1:1 CHCl3

Sources & evidence

ORD record
ord-c8a63282fc0d46fe966eb4d27f0c5791
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

Loading…