Benzyloxycarbonyl-L-phenylalanine → HCID 15391224, compound

HRID 618741Notes

Reaction equation

HRID 618741 reaction equation
C(O[C:9]([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:10])C1C=CC=CC=1.[CH2:25]([O:32][C:33]([NH:35][C@H:36](C(O)=O)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CO.O1CCCC1.[C].[Pd].C(OCC)(=O)C>[CH2:25]([O:32][C:33]([NH:35][C@H:36]([C:9]([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:10])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

9

Reactant 4

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12338838HCID 12338838, compound

Product 1

HCID 15391224HCID 15391224, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzyloxycarbonyl-(L)-tryptophanol (0.974 g) in methanol (10 ml), palladium-carbon (10%, 0.195 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 and N-benzyloxycarbonyl-(L)-phenylalanine (0.90 g) were dissolved in tetrahydrofuran (THF) (20 ml), and 1-hydroxybenzotriazole (HOBt) (0.506 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCD.HCl) (0.69 g) were added at 0° C. After stirring at room temperature for 21 hours, the reaction mixture was poured over ethyl acetate. The ethyl acetate 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 (2:1) to yield N-benzyloxycarbonyl-(L)-phenylalanyl-(L)-tryptophanol (0.878 g, 62%).

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. washThe ethyl acetate layer was washed by sequential additions of a 10% aqueous citric acid solution
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated saline and then dried (MgSO4)
  7. distillationAfter the solvent was distilled off
  8. washeluted with ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-e9eb6f1fb0be44918d6d1ec2314fcde5
Source dataset
uspto-grants-1999_09
Patent number
US05955491

Reaction notes

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