Alanine methyl ester hydrochloride → HCID 54712169, compound

HRID 908557Notes

Reaction equation

HRID 908557 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:14])[C:4](=[O:15])[C:3]=1[C:16]([O:18]C)=O.Cl.[CH3:21][O:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25]>O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:14])[C:4](=[O:15])[C:3]=1[C:16]([NH:25][C@@H:24]([CH3:26])[C:23]([O:22][CH3:21])=[O:27])=[O:18]

Participants

4

Reactant 2

HCID 2733257Alanine methyl ester hydrochlorideHCID 59340132HCID 59340132, compound

Product 1

HCID 54712169HCID 54712169, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

In a 35 mL sealed vial under N2 was suspended methyl 4-hydroxy-8-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (0.50 g, 1.9 mmol) in 1,4-dioxane (15 mL). To this solution was added L-alanine methyl ester hydrochloride (0.29 g, 2.1 mmol) and the reaction mixture was stirred at 120° C. overnight (18 h). The solution was removed from the heat and filtered over a fine frit funnel to remove any undissolved starting material. The filtrate was concentrated in vacuo and the remaining precipitate was suspended in Et2O, filtered and washed with Et2O and dried to provide a light yellow solid. Yield=0.40 g, 63%.

Workup

  1. customIn a 35 mL sealed vial under N2
  2. customThe solution was removed from the
  3. temperatureheat
  4. filtrationfiltered over a fine frit funnel
  5. customto remove
  6. concentrationThe filtrate was concentrated in vacuo
  7. filtrationfiltered
  8. washwashed with Et2O
  9. customdried
  10. customto provide a light yellow solid

Sources & evidence

ORD record
ord-74733c73d353409d9e27ee53d6969b0d
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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