1-Hydroxybenzotriazole → HCID 22877895, Verbindung

HRID 1488854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488854
Cl.[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C=CC2N(O)N=[N:33]C=2C=1.[NH:37]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][C:39](O)=[O:40]>CN(C)C=O.O.C(N(CC)CC)C>[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:42]([NH:37][CH2:38][C:39]([NH2:33])=[O:40])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]

Komponenten

7

Edukt 3

HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9976854(E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride

Produkt 1

HCID 22877895HCID 22877895, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Seven-hundred milligrams (1.86 mmols) of (E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride, 478 mg of WSCI, 375 mg of HOBt.H2O and 486 mg of Boc-Gly were dissolved in 100 ml of N,N-dimethylformamide, and 0.35 ml of triethylamine were added thereto. The mixture was reacted at 50° C. for 3.5 hours. Seven-hundred milliliters of water were added thereto, and the resulting mixture was extracted with ethyl acetate. Subsequently, the ethyl acetate layer was washed three times with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, ether), and then dissolved in a small amount of dichloromethane. Diethyl ether was added thereto for crystallization to obtain 1.71 mmols of the final product in a yield of 92%.

Aufarbeitung

  1. customThe mixture was reacted at 50° C. for 3.5 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washSubsequently, the ethyl acetate layer was washed three times with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified
  7. dissolutiondissolved in a small amount of dichloromethane
  8. additionDiethyl ether was added
  9. customfor crystallization

Quellen und Nachweise

ORD-Eintrag
ord-e6007c51b44d4833ab3b9511bdb036c1
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674906

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