Sodium Glycinate → HCID 178487719, compound

HRID 1746178Notes

Reaction equation

HRID 1746178 reaction equation
C(O[C:4]([C:6]1[C:7](=[O:19])[S:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH3:18])[CH:10]=2)=[O:5])C.[NH2:20][CH2:21][C:22]([O-:24])=[O:23].[Na+]>COCCO>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[S:8][C:7](=[O:19])[C:6]=1[C:4]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:5]

Participants

4

Reactant 2

HCID 4684308Sodium GlycinateHCID 178470016HCID 178470016, compound

Product 1

HCID 178487719HCID 178487719, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 4-hydroxy-7-methoxy-2-oxo-2H-thiochromene-3-carboxylic acid ethyl ester (47 mg, 0.17 mmol) and sodium glycinate (81 mg, 0.84 mmol) in 2-methoxyethanol (5.6 mL) was refluxed overnight (20 h). The reaction mixture was concentrated, and the crude residue dissolved in water (60 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-methoxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid (41 mg). MS ESI(−) m/e: 308.06 (M−1).

Workup

  1. temperaturewas refluxed overnight (20 h)
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe crude residue dissolved in water (60 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-45ed429a3e294c9baee557f72cc8c922
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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