Glycine → HCID 85759969, compound

HRID 2190901Notes

Reaction equation

HRID 2190901 reaction equation
CO[C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4].[NH2:17][CH2:18][C:19]([OH:21])=[O:20].C[O-].[Na+]>CN(C=O)C>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][C:6](=[O:16])[C:5]=1[C:3]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:4]

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 54706330Methyl 4-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate

Product 1

HCID 85759969HCID 85759969, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (150 mg, 0.68 mmol) in DMF (12 mL) was added glycine (1.03 g, 13.6 mmol) and NaOMe (0.5 M in MeOH, 20.4 mL, 10.2 mmol) at rt. It was concentrated in an evaporator to remove most MeOH solvent. The resulting mixture was refluxed for 2 h. After cooled, it was diluted with water (100 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo. Crude solid was triturated in hexanes, and solid product was collected and dried to give the title compound (76 mg). MS ESI(+) m/e: 264 (M+1).

Workup

  1. concentrationIt was concentrated in an evaporator
  2. customto remove most MeOH solvent
  3. temperatureThe resulting mixture was refluxed for 2 h
  4. temperatureAfter cooled
  5. additionit was diluted with water (100 mL)
  6. customPrecipitate was collected
  7. washrinsed with water
  8. customdried in vacuo
  9. customCrude solid was triturated in hexanes
  10. customsolid product was collected
  11. customdried

Sources & evidence

ORD record
ord-117561f53e5046edb49a75528d663432
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

Loading…