Sodium Glycinate → HCID 178422967, compound

HRID 1746187Notes

Reaction equation

HRID 1746187 reaction equation
CO[C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH3:16])[CH:9]=2)=[O:4].[NH2:18][CH2:19][C:20]([O-:22])=[O:21].[Na+]>COCCO>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([CH3:16])=[CH:11][CH:12]=2)[S:7][C:6](=[O:17])[C:5]=1[C:3]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:4]

Participants

4

Reactant 2

HCID 4684308Sodium GlycinateHCID 178498939HCID 178498939, compound

Product 1

HCID 178422967HCID 178422967, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 4-hydroxy-7-methyl-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (80 mg, 0.32 mmol) and sodium glycinate (310 mg, 3.2 mmol) in 2-methoxyethanol (10 mL) was refluxed for 3 h. The reaction mixture was concentrated and the crude residue dissolved in water (50 mL), acidified to pH 3-4 using 1 N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to provide [(4-hydroxy-7-methyl-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid (89 mg). MS ESI(−) m/e: 292.12 (M−1).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe crude residue dissolved in water (50 mL)
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4da05eece0c849b58f811537a00ec1d2
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

Loading…