L-Alanine → HCID 54746592, compound

HRID 2190942Notes

Reaction equation

HRID 2190942 reaction equation
CO[C:3]([C:5]1[C:6](=[O:25])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:11]=[CH:10][CH:9]=2)=[O:4].[NH2:26][C@H:27]([C:29]([OH:31])=[O:30])[CH3:28].C[O-].[Na+]>COCCO>[CH:20]1([CH2:19][CH2:18][CH2:17][O:16][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[C:14]([OH:15])=[C:5]([C:3]([NH:26][C@@H:27]([CH3:28])[C:29]([OH:31])=[O:30])=[O:4])[C:6](=[O:25])[O:7]3)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 86649474HCID 86649474, compound

Product 1

HCID 54746592HCID 54746592, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 5-(3-cyclopentyl-propoxy)-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (110 mg, 0.32 mmol) and L-alanine (424 mg, 4.76 mmol) in 2-methoxyethanol (9 mL) was added sodium methoxide (207 mg, 3.84 mmol). Resulting mixture was refluxed overnight and concentrated. Residue was dissolved in water (75 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. Organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated to provide the title compound (99.4 mg). MS ESI(−) m/e: 402.10 (M−1).

Workup

  1. customResulting mixture
  2. temperaturewas refluxed overnight
  3. concentrationconcentrated
  4. dissolutionResidue was dissolved in water (75 mL)
  5. extractionextracted with (1/1) EtOAc/hexanes which
  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-8d7c9000693f4e9894089bb6da40aa6b
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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