Sodium Glycinate → HCID 54746593, compound

HRID 2190944Notes

Reaction equation

HRID 2190944 reaction equation
CO[C:3]([C:5]1[C:6](=[O:23])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:9]=2)=[O:4].[NH2:24][CH2:25][C:26]([O-:28])=[O:27].[Na+]>COCCO>[CH:17]1([O:16][C:10]2[CH:9]=[C:8]3[C:13]([C:14]([OH:15])=[C:5]([C:3]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:4])[C:6](=[O:23])[O:7]3)=[CH:12][CH:11]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 4684308Sodium GlycinateHCID 86649475HCID 86649475, compound

Product 1

HCID 54746593HCID 54746593, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a mixture of 7-cyclohexyloxy-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (90 mg, 0.28 mmol) and sodium glycinate (275 mg, 2.83 mmol) in 2-methoxyethanol was microwaved at 150° C. for 1 h and then concentrated. Residue was dissolved in water (60 mL) and extracted with (1/1) EtOAc/hexanes which was discarded. The aqueous layer was acidified using 1 N HCl to pH=3-4 and extracted with EtOAc (2×). Combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound (82 mg). MS ESI(−) m/e: 360.06 (M−1).

Workup

  1. customwas microwaved at 150° C. for 1 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (60 mL)
  4. extractionextracted with (1/1) EtOAc/hexanes which
  5. extractionextracted with EtOAc (2×)
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-485e6b8a883241d2a2ec13a2bba60ae2
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

Loading…