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

HRID 11859

反応式

HRID 11859 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-65c497fe5d834364a584b9d25bebadc4
出典データセット
uspto-grants-2006_08
特許番号
US07098215B2

関連ノート

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