HCID 178426084, compound → HCID 178423904, compound

HRID 1746206Notes

Reaction equation

HRID 1746206 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[S:8][C:7](=[O:13])[C:6]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[C:5]2[OH:21]>[OH-].[Na+].O.[Pd]>[OH:21][C:5]1[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=[CH:2][CH:3]=2)[S:8][C:7](=[O:13])[C:6]=1[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]

Participants

5

Reactant 1

HCID 178426084HCID 178426084, compound

Product 1

HCID 178423904HCID 178423904, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

[(6-Chloro-4-hydroxy-8-methyl-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid (95 mg, 0.29 mmol) was dissolved in 1N sodium hydroxide (1.16 mL) and water (1.84 mL). 10% Palladium on carbon (9.5 mg) was added and the solution was vacuum purged and treated with hydrogen gas (1 atm). The reaction stirred overnight (18 h) at ambient temperature and the crude mixture was filtered through Celite® and the filter cake was washed with 1N sodium hydroxide. The aqueous phase was acidified to pH 3 with 1N hydrochloric acid and the product was collected by filtration to give [(4-hydroxy-8-methyl-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid (75 mg, 88%). MS ESI(+) m/e: 392.22 (M−1).

Workup

  1. custompurged
  2. additiontreated with hydrogen gas (1 atm)
  3. filtrationthe crude mixture was filtered through Celite®
  4. washthe filter cake was washed with 1N sodium hydroxide
  5. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-7903161fb49549649c328629567637cb
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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