Triethylamine → HCID 86595326, compound

HRID 899952Notes

Reaction equation

HRID 899952 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6])[CH3:2].C(N(CC)CC)C.[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>Cl.ClCCl>[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][NH:6][C@@H:5]([CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:8])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76507L-Alanine ethyl esterHCID 780724-Quinolinecarboxaldehyde

Product 1

HCID 86595326HCID 86595326, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2 g of L-alanine ethyl ester in hydrochloride form and 1.83 ml of triethylamine in 30 ml of dichloromethane is stirred at room temperature for 10 minutes. Next, 2.05 g of quinoline-4-carbaldehyde are added. The reaction medium is stirred at room temperature for 15 hours and then concentrated under reduced pressure. 35 ml of ethanol are then added; the solution is cooled to 0° C. and 0.49 g of sodium borohydride is then added portionwise. Stirring is continued for 15 hours at room temperature. The precipitate formed is filtered off; the filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography on a column (SiO2, CH2Cl2/MeOH, 95/5 by volume as eluent, Ar). 0.71 g of ethyl (S)-2-[(quinol-4-ylmethyl)amino]propanoate is obtained in the form of a pink oil.

Workup

  1. stirringThe reaction medium is stirred at room temperature for 15 hours
  2. concentrationconcentrated under reduced pressure
  3. addition35 ml of ethanol are then added
  4. temperaturethe solution is cooled to 0° C.
  5. addition0.49 g of sodium borohydride is then added portionwise
  6. stirringStirring
  7. waitis continued for 15 hours at room temperature
  8. customThe precipitate formed
  9. filtrationis filtered off
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue is purified by flash chromatography on a column (SiO2, CH2Cl2/MeOH, 95/5 by volume as eluent, Ar)

Sources & evidence

ORD record
ord-7d946731e6fb4b6687f6b3528ac91760
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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