D-Tryptophan → HCID 22855681, compound

HRID 1757296Notes

Reaction equation

HRID 1757296 reaction equation
[N:1]1([C:8]([NH:10][C@H:11]([C:16]([OH:18])=O)[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:19][C@@H:20]([C:31]([OH:33])=[O:32])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1.[CH:34]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[CH3:34][O:32][C:31](=[O:33])[C@@H:20]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[NH:19][C:16](=[O:18])[C@H:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[NH:10][C:8]([N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:9]

Participants

7

Reactant 4

HCID 9060D-TryptophanHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

Product 1

HCID 22855681HCID 22855681, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The compound obtained in (2) (1.08 g) and DTrp-Ome.Hcl (1.02 g) were dissolved in DMF (10 ml), and TEA (0.57 ml), HOBT.H2O (613 mg) and EDCI.HCl (805 mg) were added at 0°~5° C. The reaction mixture was stirred at 0°~5° C. for 1.5 h and at room temperature for 4 h. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with 1N HCl and sat. NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by MPLC (Merck, LiChroprep Si 60) with dichloromethane/methanol=30/1 for elution to give the product (1.55 g) as a colorless powder.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with 1N HCl and sat. NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by MPLC (Merck, LiChroprep Si 60) with dichloromethane/methanol=30/1 for elution

Sources & evidence

ORD record
ord-0edaaef06f1a442db1b951300203a222
Source dataset
uspto-grants-1995_08
Patent number
US05444152

Reaction notes

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