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

HRID 11859

반응식

HRID 11859 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-65c497fe5d834364a584b9d25bebadc4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098215B2

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