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Tryptamine → Nalpha-Fmoc-Ndelta-Cbz-L-ornithine 2-(3-indolyl)ethylamide

HRID 11859
Notes
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Reaction equation

HRID 11859 reaction equation
[C:1]([NH:18][C@H:19]([C:34](O)=[O:35])[CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:59][CH2:60][CH2:61][C:62]1[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[NH:64][CH:63]=1>CN(C=O)C>[NH:64]1[C:65]2[C:70](=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:62]([CH2:61][CH2:60][NH:59][C:34](=[O:35])[C@H:19]([CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[NH:18][C:1]([O:3][CH2:4][CH:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]3[C:17]2=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:2])=[CH:63]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1150TryptamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14999635Fmoc-orn(Z)-OH

Product 1

HCID 86592267Nalpha-Fmoc-Ndelta-Cbz-L-ornithine 2-(3-indolyl)ethylamide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Commercially available Nα-Fmoc-Nδ-Cbz-L-ornithine (528.0 mg) was dissolved in DMF (10.6 ml), and HOBt (235 mg), WSCI hydrochloride (334 mg), and tryptamine (0.165 ml) were added to the solution. The mixture was stirred for 16 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform and extracted with 1 mol/l aqueous solution of hydrochloric acid. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate. The solvent was removed by distillation and the residue was purified by silica gel column chromatography (50 g, chloroform/ethyl acetate=1/1) to obtain the title compound (690 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted with 1 mol/l aqueous solution of hydrochloric acid
  5. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  6. customThe solvent was removed by distillation
  7. customthe residue was purified by silica gel column chromatography (50 g, chloroform/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-65c497fe5d834364a584b9d25bebadc4
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098215B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes