L-Alanine → HCID 54746594, compound

HRID 2190945Notes

Reaction equation

HRID 2190945 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][C@H:25]([C:27]([OH:29])=[O:28])[CH3:26].C[O-].[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][C@@H:25]([CH3:26])[C:27]([OH:29])=[O:28])=[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

5

Reactant 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 86649475HCID 86649475, compound

Product 1

HCID 54746594HCID 54746594, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 7-cyclohexyloxy-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (80 mg, 0.25 mmol), L-alanine (224 mg, 2.5 mmol) and sodium methoxide (108 mg, 2 mmol) in 2-methoxyethanol (3.5 mL) was microwaved at 150° C. for 2 h and then concentrated. Residue was dissolved in water (70 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 (68 mg). MS ESI(−) m/e: 374.07 (M−1).

Workup

  1. customwas microwaved at 150° C. for 2 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (70 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-a351f1b234224fbda89ff86e35dc1c0c
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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