Syringic Acid → HCID 18510866, Verbindung

HRID 1370545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1370545
[C:1]([OH:14])(=O)[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH:38]1([N:44]2[CH2:52][C:51]3[C:46](=[CH:47][C:48]([N:53]4[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]4)=[CH:49][CH:50]=3)[C:45]2=[O:59])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.[Cl-].[NH4+]>CN(C=O)C.C(N(CC)CC)C>[CH:38]1([N:44]2[CH2:52][C:51]3[C:46](=[CH:47][C:48]([N:53]4[CH2:54][CH2:55][N:56]([C:1](=[O:14])[C:2]5[CH:3]=[C:4]([O:5][CH3:6])[C:7]([OH:8])=[C:9]([O:10][CH3:11])[CH:12]=5)[CH2:57][CH2:58]4)=[CH:49][CH:50]=3)[C:45]2=[O:59])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Komponenten

8

Edukt 5

HCID 10742Syringic AcidHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22180413HCID 22180413, Verbindung

Produkt 1

HCID 18510866HCID 18510866, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of syringic acid (20 mg) in dry DMF (2 ml) was cooled to 0° C. 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (WSCI) and 1-hydroxybenztriazole hydrate (HOBt) were added thereto in that order. The mixture was stirred at 0° C. for one hr. The compound (30 mg) obtained in step (e) of Example 1 and triethylamine were added thereto in that order. The mixture was stirred at 0° C. for one hr, and then stirred at room temperature overnight. A saturated aqueous ammonium chloride solution(5 ml) was added thereto, followed by separation with ethyl acetate and water. The ethyl acetate layer was washed with an aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under the reduced pressure. The residue was purified by chromatography on silica gel (chloroform:methanol=20:1) to give 42 mg of the title compound.

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for one hr
  2. stirringstirred at room temperature overnight
  3. customfollowed by separation with ethyl acetate and water
  4. washThe ethyl acetate layer was washed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under the reduced pressure
  7. customThe residue was purified by chromatography on silica gel (chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-bbe6e7d44a194c888a6d893446094ab4
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583144B2

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