Triethylamine → HCID 178439611, Verbindung

HRID 54856

Reaktionsgleichung

Reaktionsgleichung von HRID 54856
[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.FC1C(O)=C(F)C(F)=C(F)C=1F.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.Cl.[NH2:62][CH2:63][CH2:64][C:65]1[N:69]=[CH:68][NH:67][CH:66]=1>C(OCC)(=O)C.CN(C)C=O>[NH:67]1[CH:66]=[C:65]([CH2:64][CH2:63][NH:62][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])[N:69]=[CH:68]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophanHCID 178478691HCID 178478691, Verbindung

Produkt 1

HCID 178439611HCID 178439611, VerbindungAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry ethyl acetate (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added pentafluorophenol (0.189 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.200 g, 1.04 mmol). This mixture was stirred 2 hours, then triethylamine (0.36 mL, 2.6 mmol) and histamine dihydrochloride (0.240 g, 1.30 mmol) were added. After stirring an additional 40 hours, the resulting mixture was diluted with ethyl acetate (20 mL), and washed with water. The organic phase was dried over MgSO4, concentrated, purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant), and dried for 48 hours under vacuum at 70° C. to provide 0.234 g (47%) of product; 1H NMR (CDCl3) δ1.40-1.60 (2H, m), 1.57 (3H, s), 1.65-2.00 (13H, m), 2.65-2.75 (2H, m), 3.25-3.45 (4H, m), 4.82 (1H, br s), 5.42 ([H, br s), 6.67 (1H, s), 6.81 (1H, br s), 6.91 (1H, br s),7.00-7.20 (2H, m), 7.34 (1H, d, J 7 Hz), 7.46 (1H, s), 7.55 (1H, d, J 7 Hz), 8.67 (1H, br s).

Aufarbeitung

  1. stirringAfter stirring an additional 40 hours
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant)
  6. customdried for 48 hours under vacuum at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-85cef224fcff45b1b389493bd1530816
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622983

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