Triethylamine → HCID 53972264, Verbindung

HRID 652419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652419
[F:1][C:2]([F:24])([F:23])[C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:15](=[S:22])[N:16]([CH3:21])[CH2:17][C:18]([OH:20])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.[OH:55][CH:56]1[O:64][C@H:63]([CH2:65][OH:66])[C@@H:61]([OH:62])[C@H:59]([OH:60])[C@H:57]1[NH2:58]>CN(C)C=O>[CH3:14][O:13][C:12]1[C:3]([C:2]([F:1])([F:23])[F:24])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:15]([N:16]([CH2:17][C:18]([NH:58][C@H:57]([C@H:59]([C@@H:61]([C@@H:63]([CH2:65][OH:66])[OH:64])[OH:62])[OH:60])[CH:56]=[O:55])=[O:20])[CH3:21])=[S:22])=[CH:7][CH:6]=[CH:5]2

Komponenten

7

Edukt 5

HCID 8471Triethylamine2×HCID 53359TolrestatHCID 757711-HydroxybenzotriazoleHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 53972264HCID 53972264, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-[[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine (3.57 g, 0.010 mol), 1-hydroxybenzotriazole (2 g, 0.015 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.3 g, 0.012 mol) and triethylamine (3.5 mol, 0.025 mol) were dissolved in dimethylformamide (25 ml). The mixture was cooled in ice and stirred for 1 hour. D-Glucosamine hydrochloride (2.38 g, 0.011 mol), and additional triethylamine (2.0 mol) were added to the cold reaction mixture. The reaction mixture was stirred at 0° C. for 1 hour, and at room temperature over night and evaporated. The residue was triturated with water and filtered. The solids were washed with H2O, 1NHCl, 5% NaHCO3, H2O and crystallized from 8/5 H2O/MeOH to yield 3.63 g, 67.7%. The product was further purified by recrystallization from boiling methanol (3.1 g), m.p. 166°-169° C. (dec.) as yellow crystals.

Aufarbeitung

  1. temperatureThe mixture was cooled in ice
  2. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  3. waitat room temperature over night
  4. customevaporated
  5. customThe residue was triturated with water
  6. filtrationfiltered
  7. washThe solids were washed with H2O
  8. custom1NHCl, 5% NaHCO3, H2O and crystallized from 8/5 H2O/MeOH
  9. customto yield 3.63 g, 67.7%
  10. customThe product was further purified by recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-428faeae9ded4521a0843733d7c742dc
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04672059

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