Sulfuric acid magnesium salt (1:1) → HCID 55251614, compound

HRID 899953Notes

Reaction equation

HRID 899953 reaction equation
Cl.[NH2:2][C:3]([CH3:9])(C)[C:4]([O:6][CH3:7])=[O:5].S([O-])([O-])(=O)=O.[Mg+2].[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]=O)=[CH:18][CH:17]=1.[BH4-].[Na+]>ClCCl.C(N(CC)CC)C>[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][NH:2][CH:3]([CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 780724-QuinolinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 55251614HCID 55251614, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.5 g of methyl α-aminoisobutyrate hydrochloride and 1.4 ml of triethylamine in 30 ml of dichloromethane is stirred at 0° C. for 20 minutes. Next, 1 g of magnesium sulfate and 1.5 g of quinoline-4-carbaldehyde are added. Stirring is continued for 15 hours at room temperature and the mixture is then concentrated under reduced pressure. The residue is taken up in 35 ml of methanol and the solution obtained is cooled to 0° C. 0.4 g of sodium borohydride is added portionwise and stirring is continued at room temperature for 15 hours. The precipitate formed is filtered and the filtrate is concentrated under reduced pressure. The residue obtained is purified by recrystallization from diisopropyl ether. 600 mg of the expected product are obtained in the form of a pink oil.

Workup

  1. stirringStirring
  2. waitis continued for 15 hours at room temperature
  3. concentrationthe mixture is then concentrated under reduced pressure
  4. customthe solution obtained
  5. temperatureis cooled to 0° C
  6. stirringstirring
  7. waitis continued at room temperature for 15 hours
  8. customThe precipitate formed
  9. filtrationis filtered
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue obtained
  12. customis purified by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-027ed2065b8f46449de3cc20d5e9fa14
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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