Hydrochloric Acid → HCID 54746577, compound

HRID 2190929Notes

Reaction equation

HRID 2190929 reaction equation
CO[C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([Cl:16])[CH:9]=2)=[O:4].[NH2:18][C@H:19]([C:21]([OH:23])=[O:22])[CH3:20].C[O-].[Na+].Cl>COCCO>[Cl:16][C:10]1[CH:9]=[C:8]2[C:13]([C:14]([OH:15])=[C:5]([C:3]([NH:18][C@@H:19]([CH3:20])[C:21]([OH:23])=[O:22])=[O:4])[C:6](=[O:17])[O:7]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 86649470HCID 86649470, compound

Product 1

HCID 54746577HCID 54746577, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 125 mg of 7-chloro-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (0.5 mmol), 534 mg of L-alanine (6 mmol), and 270 mg of sodium methoxide (5 mmol) in 8 mL of 2-methoxyethanol was heated at reflux for 18 hours. The mixture was cooled and acidified with 20 mL of 1 N HCl to precipitate a white solid. The solid was collected on a glass fitted filter, washed twice with water, and dried under vacuum to 129 mg of a white solid. MS: (+) m/z 313.96/311.95 (M+1, 35/37Cl)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. customto precipitate a white solid
  5. customThe solid was collected on a glass
  6. customfitted
  7. filtrationfilter
  8. washwashed twice with water
  9. dry with materialdried under vacuum to 129 mg of a white solid

Sources & evidence

ORD record
ord-3880f74b23df468cb2ddb793d7e215cd
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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