L-Alanine methyl ester → HCID 54211748, compound

HRID 1729089Notes

Reaction equation

HRID 1729089 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C@H:4]([CH3:6])[NH2:5].[Li+].CC([N-]C(C)C)C.CS(C[C:21]1[N:22]=[CH:23][C:24]2[N:25]([S:34]([CH3:37])(=[O:36])=[O:35])[C:26]3[C:31]([C:32]=2[CH:33]=1)=[CH:30][CH:29]=[CH:28][CH:27]=3)(=O)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:7])[C@:4]([C:21]1[N:22]=[CH:23][C:24]2[N:25]([S:34]([CH3:37])(=[O:35])=[O:36])[C:26]3[C:31]([C:32]=2[CH:33]=1)=[CH:30][CH:29]=[CH:28][CH:27]=3)([CH3:6])[NH2:5]

Participants

5

Reactant 3

HCID 82335L-Alanine methyl esterHCID 2724682Lithium diisopropylamideHCID 19013532HCID 19013532, compound

Product 1

HCID 54211748HCID 54211748, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-76 °C

Procedure

The Schiffs' base (1.34 g, 7.0 mmol), derived from alanine methyl ester andbenzaldehyde was dissolved in THF (25 mL), and cooled to -76° C. To this was added a solution of LDA (11.6 mL of 10% in n-hexane) in THF (15 mL). After stirring for 30 minutes this solution was treated with 3-(methylsulfonylmethyl)-9-methylsulfonyl-β-carboline (25 Ml in THF) from Step 2, warmed to room temperature and stirred over night. The brown suspension was evaporated in vacuum, the residue dissolved in ethyl acetate and the solution was washed with water, combined with 100 mL 1N HCl and was stirred for 1 hour at room temperature. The organic layer was separated and the aqueous solution was treated with Na2CO3 to pH 8-9. This was extracted with ethyl acetate (2×100 mL), dried overNa2SO4 and the organic solvent was evaporated in vacuum. The residue was flash chromatographed on silica gel using 5% methanol/methylene chloride to yield 2-[9-(methylsulfonyl)-β-carbolin-3-yl]-alanine methyl ester (0.53 g, 21.2%) as a yellow oil.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred over night
  3. customThe brown suspension was evaporated in vacuum
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. stirringwas stirred for 1 hour at room temperature
  7. customThe organic layer was separated
  8. additionthe aqueous solution was treated with Na2CO3 to pH 8-9
  9. extractionThis was extracted with ethyl acetate (2×100 mL)
  10. customdried overNa2SO4 and the organic solvent
  11. customwas evaporated in vacuum
  12. customchromatographed on silica gel using 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-68b890091bf44b389f657435a08a2403
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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