HCID 66756613, compound → HCID 66756638, compound

HRID 1642628Notes

Reaction equation

HRID 1642628 reaction equation
[K:1].C([O:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[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]>[K:1].[OH:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:13]=[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 66756613HCID 66756613, compound

Product 1

HCID 66756638HCID 66756638, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 5-(2-benzyloxy-4-phenoxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt (0.30 g, 0.67 mmol) in water (10 mL) is hydrogenated at 1 atm over 10% Pd/C (0.05 g) for 24 h. The catalyst is filtered and the water removed by lyophilization to afford the product, 5-(2-hydroxy-4-phenoxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt, as an amorphous pale-grey solid: mp=205-210° C.; 1H NMR (DMSO-d6) δ 9.52 (br s, 1H), 7.47-7.41 (m, 3H), 7.19 (t, 1H), 7.08 (d, J=7.57 Hz, 2H), 6.51 (d, J=2.78 Hz, 1H), 6.46 (dd, J=8.59, 2.78 Hz, 1H), 4.06 (s, 2H); MS (M−H)−=319.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe water removed by lyophilization

Sources & evidence

ORD record
ord-bbc47d620dc543248bcea4613867e372
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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