Tryptamine → Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[2-[[2-(1H-indol-3-yl)ethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

HRID 54849

Reaktionsgleichung

Reaktionsgleichung von HRID 54849
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([NH:14][C:15]([CH3:29])([C:26](O)=[O:27])[CH2:16][C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[O:13])[CH2:8]2.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:56][CH2:57][CH2:58][C:59]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[NH:61][CH:60]=1>CCOC(C)=O>[NH:61]1[C:62]2[C:67](=[CH:66][CH:65]=[CH:64][CH:63]=2)[C:59]([CH2:58][CH2:57][NH:56][C:26](=[O:27])[C:15]([NH:14][C:12](=[O:13])[O:11][CH:2]2[CH:1]3[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]2[CH2:4]4)[CH2:8]3)([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH3:29])=[CH:60]1

Komponenten

6

Edukt 4

HCID 1150TryptamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophan

Produkt 1

HCID 86747492Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[2-[[2-(1H-indol-3-yl)ethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.19 g (1.41 mmol) of 1-hydroxybenzotriazole hydrate in 20 mL of anhydrous EtOAc (under a N2 atmosphere) was treated in one portion with 0.34 g (1.65 mmol) of 1,3-dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 2 hours, treated with 0.26 g (1.62 mmol) of tryptamine, and stirred for an additional 18 hours. The precipitated solid was filtered, washed with a small amount of fresh EtOAc, and discarded. The filtrate was diluted to 150 mL with EtOAc and washed with 5% aqueous citric acid (3×150 mL), brine (1×150 mL), 5% aqueous NaHCO3 (3×150 mL), and brine again. The organic layer was dried (Na2SO4) and evaporated (vacuum) to a tan solid. The residue was chromatographed (E. Merck prepacked Lobar column, 37×440 mm, eluted with 2% MeOH in CH2Cl2) to yield the purified product as a white foam, 0.32 g (47%); 1H NMR (CDCl3) δ1.46-1.92 (17H, m), 2.83 (2H, t, J 7 Hz), 3.23 (1H, d, J 15 Hz), 3.40 (1H, d, J 15 Hz), 3.52 (2H, m), 4.78 (1H, br s), 5.23 (1H, br s), 6.12 (1H, m), 6.77 (1H, m), 6.82 (1H, m), 7.06-7.58 (8H, m), 7.96 (2H, br s).

Aufarbeitung

  1. stirringstirred for an additional 18 hours
  2. filtrationThe precipitated solid was filtered
  3. washwashed with a small amount of fresh EtOAc
  4. additionThe filtrate was diluted to 150 mL with EtOAc
  5. washwashed with 5% aqueous citric acid (3×150 mL), brine (1×150 mL), 5% aqueous NaHCO3 (3×150 mL), and brine again
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated (vacuum) to a tan solid
  8. customThe residue was chromatographed
  9. wash(E. Merck prepacked Lobar column, 37×440 mm, eluted with 2% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-26b2eb065c6f4b64a30f885e4b2c2c25
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622983

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