HCID 86624030, compound → HCID 17751505, compound

HRID 643954Notes

Reaction equation

HRID 643954 reaction equation
[K].C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([O:21][CH3:22])[C:16](=[O:20])[O:17]2)=[CH:12][C:11]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1)C1C=CC=CC=1>O.[Pd]>[OH:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([O:21][CH3:22])[C:16](=[O:20])[O:17]2)=[CH:12][C:11]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1

Participants

4

Reactant 1

HCID 86624030HCID 86624030, compound

Product 1

HCID 17751505HCID 17751505, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of 5-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt in water (10 mL), is added 10% Pd/C (0.014 g). The suspension is stirred under an atmosphere of H2 for 18 h. The aqueous solution is filtered through Celite and the water is removed by lyophilization. The crude solid is purified by preparative HPLC to afford 5-(7-hydroxy-3-methoxy-2-oxo-2H-chromen-6-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a pale-yellow powder: 1H NMR (DMSO-d6) δ 7.66 (s, 1H), 7.27 (s, 1H), 6.77 (d, J=3.54 Hz, 1H), 4.03 (s, 2H), 3.77 (s, 3H); (M−H)−=325.

Workup

  1. filtrationThe aqueous solution is filtered through Celite
  2. customthe water is removed by lyophilization
  3. customThe crude solid is purified by preparative HPLC

Sources & evidence

ORD record
ord-afcf00e1b6194b75897faa71943889ef
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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