Benzaldehyde → HCID 54300931, compound

HRID 1729092Notes

Reaction equation

HRID 1729092 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C@H:4]([CH3:6])[NH2:5].C(=O)C1C=CC=CC=1.CC(C)([O-])C.[K+].Cl.ClC[C:25]1[CH:37]=[C:36]2[C:28](=[N:29][C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:27][N:26]=1>C1COCC1>[CH3:1][O:2][C:3](=[O:7])[C@:4]([C:25]1[N:26]=[CH:27][C:28]2[NH:29][C:30]3[C:35]([C:36]=2[CH:37]=1)=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:6])[NH2:5]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 82335L-Alanine methyl esterHCID 19013533HCID 19013533, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54300931HCID 54300931, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In THF (85 mL) was dissolved the Schiffs' Base (2.45 g, 12.8 mmol), derivedfrom alanine methyl ester and benzaldehyde, and cooled to -40° C. Tothis was added potassium-t-butoxide (2.92 g, 26 mmol) and the orange solution stirred under nitrogen at -40° C. for 30 minutes. To this was added 3-(chloromethyl)-1H-β-carboline hydrochloride salt (3.24 g,12.8 mmol), the reaction mixture stirred for another 30 minutes at -40° C. and then slowly warmed to room temperature overnight. The black solution was evaporated in the vacuum and then partitioned between ethyl acetate (150 mL) and water (50 mL). To the organic layer was added 1N HCl (100 mL) and the mixture was stirred for 2 hours. Then the organic was separated, washed with Na2CO3 solution, dried over Na2SO4 and evaporated in the vacuum to give 2-(9H-β-carboline-3-yl)-alanine methyl ester (2.4 g, 50.5%) as a light tan foam.

Workup

  1. stirringthe reaction mixture stirred for another 30 minutes at -40° C.
  2. temperatureslowly warmed to room temperature overnight
  3. customThe black solution was evaporated in the vacuum
  4. custompartitioned between ethyl acetate (150 mL) and water (50 mL)
  5. additionTo the organic layer was added 1N HCl (100 mL)
  6. stirringthe mixture was stirred for 2 hours
  7. customThen the organic was separated
  8. washwashed with Na2CO3 solution
  9. dry with materialdried over Na2SO4
  10. customevaporated in the vacuum

Sources & evidence

ORD record
ord-a75cf1e3a9be415293fd8f76af9fce70
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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