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

HRID 356517Notes

Reaction equation

HRID 356517 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 0.2M 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. 1 H 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-36fe17606f8c42bda69bd18a7330d9f5
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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