Sodium Glycinate → HCID 54746582, compound

HRID 2190933Notes

Reaction equation

HRID 2190933 reaction equation
CO[C:3]([C:5]1[C:6](=[O:24])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:11]=[CH:10][CH:9]=2)=[O:4].[NH2:25][CH2:26][C:27]([O-:29])=[O:28].[Na+]>COCCO>[CH2:17]([O:16][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[C:14]([OH:15])=[C:5]([C:3]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4])[C:6](=[O:24])[O:7]2)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 4684308Sodium GlycinateHCID 86649471HCID 86649471, compound

Product 1

HCID 54746582HCID 54746582, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 5-benzyloxy-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (54 mg, 0.17 mmol) and sodium glycinate (241 mg, 2.48 mmol) in 2-methoxyethanol was refluxed for 18 h and then concentrated. Residue was dissolved in water (60 mL) and acidified using 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo. Crude product was triturated with hexanes. Solid was collected and dried to provide the title compound (45 mg). MS ESI(+) m/e: 370.13 (M+1).

Workup

  1. temperaturewas refluxed for 18 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (60 mL)
  4. customPrecipitate was collected
  5. washrinsed with water
  6. customdried in vacuo
  7. customCrude product was triturated with hexanes
  8. customSolid was collected
  9. customdried

Sources & evidence

ORD record
ord-456ade0ea991468390a02e5b69540b2a
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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