Triethylamine → HCID 68684193, Verbindung

HRID 657175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657175
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH:3]1[C:15]([OH:17])=O.C([N:20](CC)CC)C.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[NH4+]>CN(C)C=O>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH:3]1[C:15]([NH2:20])=[O:17]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 14013Ammonium BicarbonateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20502081HCID 20502081, Verbindung

Produkt 1

HCID 68684193HCID 68684193, VerbindungAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxylic acid (12 g) and triethylamine (3.53 mL, 25.5 mmol) in N,N-dimethylformamide (60 mL) was added 1-hydroxy-7-azabenzotriazole (3.48 g, 25.6 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (8.54 g, 56.2 mmol). After stirring for 5-10 min. ammonium bicarbonate (15.3 g, 204 mmol) was added. The reaction mixture was stirred at room temperature for overnight. The solvent was then removed under reduced pressure and the residue was dissolved in aqueous sodium bicarbonate and dichloromethane. The aqueous phase was extracted with 9:1 dichloromethane:methanol. The organic layer was dried and evaporated. The residue was chromatographed on silica gel, eluting with 10-20% methanol/dichloromethane, to give the desired compound (4.15 g, 35%). Impure fractions were chromatographed again to give further product (1.02 g).

Aufarbeitung

  1. additionwas added
  2. customThe solvent was then removed under reduced pressure
  3. dissolutionthe residue was dissolved in aqueous sodium bicarbonate
  4. extractionThe aqueous phase was extracted with 9:1 dichloromethane
  5. customThe organic layer was dried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 10-20% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-197c2d92777b4a248c3ab1b1c83dc793
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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