Triethylamine → HCID 54361343, compound

HRID 618743Notes

Reaction equation

HRID 618743 reaction equation
C(OC([NH:11][C@H:12]([CH2:23][OH:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=O)C1C=CC=CC=1.O1CCOCC1.[C:31]1([S:41](Cl)(=[O:43])=[O:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>C(O)C.CN(C)C=O.[C].[Pd].O>[C:31]1([S:41]([NH:11][C@H:12]([CH2:23][OH:24])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)(=[O:43])=[O:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 665601-Naphthalenesulfonyl chlorideHCID 12338838HCID 12338838, compound

Product 1

HCID 54361343HCID 54361343, compoundYield 68.2%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-benzyloxycarbonyl-(L)-tryptophanol (1.0 g) in ethanol hydrogenation (20 ml)-dioxane (40 ml), palladium-carbon (5%, 0.5 g) was subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure. After the palladium-carbon was filtered off, the filtrate was concentrated under reduced pressure to yield an oily substance. This oily substance was dissolved in N,N-dimethylformamide (10 ml), and 1-naphthalenesulfonyl chloride (0.77 g) was added and then triethylamine (0.39 g) was added at 0° C. After overnight stirring at room temperature, the reaction mixture was poured over water and extracted with ether. The ether layer was washed by sequential additions of a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution and saturated saline and then dried (MgSO4). After the solvent was distilled off, the oily residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:1) to yield a powder of N-(1-naphthylsulfonyl)-(L)-tryptophanol (0.8 g, 68%).

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure
  2. filtrationAfter the palladium-carbon was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto yield an oily substance
  5. extractionextracted with ether
  6. washThe ether layer was washed by sequential additions of a 10% aqueous citric acid solution
  7. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated saline and then dried (MgSO4)
  8. distillationAfter the solvent was distilled off
  9. washeluted with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-674a9349e3494a6287319aab2fe6a268
Source dataset
uspto-grants-1999_09
Patent number
US05955491

Reaction notes

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