Triethylamine → HCID 53973617, Verbindung

HRID 1701043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1701043
[CH3:1][NH:2][C@@H:3]([C:11]1[O:15][C:14]([C:16]([NH2:18])=[O:17])=[N:13][N:12]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(OC([CH2:26][NH:27][C@H:28]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:29]([OH:31])=O)=O)(C)(C)C.ON1C2N=C[CH:51]=[CH:52][C:47]=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:65](N(CC)CC)C.[C:72]([O:75]CC)(=[O:74])C>ClCCl.CN(C=O)C.O>[C:52]([O:75][C:72](=[O:74])[N:27]([C@@H:28]([C:29](=[O:31])[N:2]([C@@H:3]([C:11]1[O:15][C:14]([C:16](=[O:17])[NH2:18])=[N:13][N:12]=1)[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:1])[CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[CH3:26])([CH3:51])([CH3:47])[CH3:65]

Komponenten

10

Edukt 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53913605HCID 53913605, VerbindungHCID 54532855HCID 54532855, Verbindung

Produkt 1

HCID 53973617HCID 53973617, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-((1R)-1-Methylamino-2-phenylethyl)-[1,3,4]oxadiazole-2-carboxylic acid amide (240 mg, 0.98 mmol), (R)-2-((tert-butoxycarbonyl)methylamino)-3-(2-naphthyl)propionic acid (320 mg, 0.98 mmol) and 1-hydroxy-7-azabenzotriazole (133 mg, 0.98 mmol) were dissolved in dichloromethane (8 ml) and DMF (4 ml). The solution was cooled to 0° C. and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (230 mg, 1.18 mmol) was added. After 10 min triethylamine (0.35 ml, 2.46 mmol) was added. The solution was stirred for lh at 0° C. and subsequently for 16 h at room temp. The solution was diluted with ethyl acetate (30 ml) and water (20 ml). The phases were separated and the aqueous phase was extracted with ethyl acetate (20 ml). The combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (30 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g) with ethyl acetate to give 301 mg of ((1R)-1-(((1R)-1-(5-carbamoyl-[1,3,4]oxadiazol-2-yl)-2-phenylethyl) methylcarbamoyl)-2-(2-naphthyl)ethyl)methylcarbamic acid tert-butylester.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (20 ml)
  3. washThe combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (30 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (50 g) with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-30b95248d315432ca45c36858513c1a2
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350767B1

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