Nitrogen → HCID 66750659, compound

HRID 643869Notes

Reaction equation

HRID 643869 reaction equation
[K:1].C([O:9][C:10]1[C:11]([N:28]2[S:32](=[O:34])(=[O:33])[NH:31][C:30](=[O:35])[CH2:29]2)=[CH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([O:20]CC1C=CC=CC=1)=[CH:15][CH:14]=2)C1C=CC=CC=1.N#N>O.[Pd]>[K:1].[OH:9][C:10]1[C:11]([N:28]2[S:32](=[O:34])(=[O:33])[NH:31][C:30](=[O:35])[CH2:29]2)=[CH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([OH:20])=[CH:15][CH:14]=2

Participants

5

Reactant 2

HCID 947NitrogenHCID 66750613HCID 66750613, compound

Product 1

HCID 66750659HCID 66750659, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of 5-(3,6-bis-benzyloxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt (0.129 g, 0.252 mmol) in H2O (5 mL), flushed with N2, is added 10% Pd/C (0.10 g). The mixture is flushed with N2 again and then placed under an atmosphere of H2. The mixture is stirred vigorously for 1.5 h before being judged complete by LC/MS. The reaction mixture is filtered over Celite. The filtrate is washed with EtOH and the aqueous layer is lyophilized overnight. The residual solid is redissolved in H2O and refiltered over Celite. The green filtrate is lyophilized again overnight. The residue is purified via prep HPLC. The desired fractions are concentrated and dissolved in a minimum amount of EtOH. To this solution is added a 0.5M solution of KHCO3 followed by the addition of H2O. The reaction mixture is stirred for 2 min and lyophilized overnight to afford 5-(3,6-dihydroxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt: 1H NMR (DMSO-d6) 9.93 (s, 1H), 9.63 (s, 1H), 7.79 (s, 1H), 7.61 (d, J=8 Hz, 1H), 7.01 (s, 1H), 6.86 (m, 2H), 4.43 (s, 2H).

Workup

  1. customThe mixture is flushed with N2 again
  2. filtrationThe reaction mixture is filtered over Celite
  3. washThe filtrate is washed with EtOH
  4. waitthe aqueous layer is lyophilized overnight
  5. dissolutionThe residual solid is redissolved in H2O
  6. waitThe green filtrate is lyophilized again overnight
  7. customThe residue is purified via prep HPLC
  8. concentrationThe desired fractions are concentrated
  9. dissolutiondissolved in a minimum amount of EtOH
  10. additionTo this solution is added a 0.5M solution of KHCO3
  11. additionfollowed by the addition of H2O
  12. stirringThe reaction mixture is stirred for 2 min
  13. waitlyophilized overnight

Sources & evidence

ORD record
ord-59995199009d418db7829f032d17d722
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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