L-Alanine → HCID 178462106, compound

HRID 1746233Notes

Reaction equation

HRID 1746233 reaction equation
CO[C:3]([C:5]1[C:6](=[O:16])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4].[NH2:17][C@H:18]([C:20]([OH:22])=[O:21])[CH3:19].C[O-].[Na+]>COCCO>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:7][C:6](=[O:16])[C:5]=1[C:3]([NH:17][C@@H:18]([CH3:19])[C:20]([OH:22])=[O:21])=[O:4]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 178498936HCID 178498936, compound

Product 1

HCID 178462106HCID 178462106, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester compound 3(c) (103 mg, 0.44 mmol), L-alanine (583 mg, 6.55 mmol) and NaOMe (285 mg, 5.28 mmol) in 2-methoxyethanol (14 mL) was refluxed for 6 h and concentrated. Residue was dissolved in water (100 mL) and acidified by 1 N HCl solution to pH=3-4. Precipitate was collected and rinsed with water. It was dried in vacuo and then triturated in MeOH (10 mL). Solid was collected and dried in vacuo to provide the title compound (57 mg). MS ESI(−) m/e: 291.12 (M−1).

Workup

  1. temperaturewas refluxed for 6 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (100 mL)
  4. customPrecipitate was collected
  5. washrinsed with water
  6. customIt was dried in vacuo
  7. customtriturated in MeOH (10 mL)
  8. customSolid was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-8006eca7b8474eceaa36c98c941a1c68
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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