Sodium Glycinate → HCID 54746544, compound

HRID 2190907Notes

Reaction equation

HRID 2190907 reaction equation
CO[C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:16])=[O:4].[Na+].[NH2:19][CH2:20][C:21]([O-:23])=[O:22]>COCCO>[Cl:16][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[O:7][C:6](=[O:17])[C:5]([C:3]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:4])=[C:14]2[OH:15]

Participants

4

Reactant 2

HCID 4684308Sodium GlycinateHCID 87431910HCID 87431910, compound

Product 1

HCID 54746544HCID 54746544, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 8-chloro-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (150 mg, 0.59 mmol) and glycine sodium salt (286 mg, 2.95 mmol) in 2-methoxyethanol (6 mL) was heated to reflux overnight. Reaction mixture was concentrated and dissolved in water (25 mL). The solution was acidified by 1 N aq HCl to pH=2-3 and extracted with EtOAc. Organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated to give the title compound (135 mg). MS ESI(−) m/e: 296 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customReaction mixture
  4. concentrationwas concentrated
  5. dissolutiondissolved in water (25 mL)
  6. extractionextracted with EtOAc
  7. washOrganic layer was washed with water, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-186595545a2e40dfac54818dc3773313
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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