L-Alanine → HCID 178462108, compound

HRID 1423961Notes

Reaction equation

HRID 1423961 reaction equation
CO[C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11]([Cl:16])=[CH:10][CH:9]=2)=[O:4].[NH2:18][C@H:19]([C:21]([OH:23])=[O:22])[CH3:20].C[O-].[Na+]>COCCO>[Cl:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[S:7][C:6](=[O:17])[C:5]([C:3]([NH:18][C@@H:19]([CH3:20])[C:21]([OH:23])=[O:22])=[O:4])=[C:14]2[OH:15]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 178498942HCID 178498942, compound2×

Product 1

HCID 178462108HCID 178462108, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 6-chloro-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (Compound 58(b)) (100 mg, 0.37 mmol), L-alanine (165 mg, 1.85 mmol) and NaOMe (80 mg, 1.48 mmol) in 2-methoxyethanol (5.2 mL) was microwaved at 150° C. for 2 h and concentrated. Residue was dissolved in water (60 mL). Insoluble solid was filtered off. The Aqueous filtrate was acidified using 1 N HCl solution to pH=3-4. Precipitate was collected and dried. It was then triturated with MeOH (2 mL). Solid was collected and dried in vacuo to provide the title compound (50 mg). MS ESI(−) m/e: 325.93 (M−1).

Workup

  1. customwas microwaved at 150° C. for 2 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (60 mL)
  4. filtrationInsoluble solid was filtered off
  5. customPrecipitate was collected
  6. customdried
  7. customIt was then triturated with MeOH (2 mL)
  8. customSolid was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5e6e8cdcb4614a3dbe3497d2b83e6d34
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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