HOAt → Tert-butyl 2-(aminocarbonyl)-4-fluorobenzylcarbamate

HRID 2252815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2252815
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:11]=1[C:12](O)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:22](C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C=O)C>[NH2:22][C:12]([C:11]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:10]=1[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13]

Komponenten

5

Edukt 3

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110654742-[[(tert-Butoxycarbonyl)amino]methyl]-5-fluorobenzoic acid

Produkt 1

HCID 59645228Tert-butyl 2-(aminocarbonyl)-4-fluorobenzylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-{[(Tert-butoxycarbonyl)amino]methyl}-5-fluorobenzoic acid (800 mg, 2.97 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (854 mg, 4.46 mmol), and 1-hydroxy-7-azabenzotriazole (607 mg, 4.46 mmol) were added to dry DMF (10 mL) and stirred for 30 minutes to preform the activated ester. Ammonia gas was bubbled through the solution for 30 seconds and the reaction was allowed to stir for 5 minutes. The solvent was removed in vacuo and the residue was purified by flash column chromatography (ISCO column, 120 g silica) running a gradient of 0-40% acetone/hexane over 35 min. The product fractions were concentrated to afford the title compound as a white solid.

Aufarbeitung

  1. customAmmonia gas was bubbled through the solution for 30 seconds
  2. stirringto stir for 5 minutes
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash column chromatography (ISCO column, 120 g silica)
  5. customover 35 min
  6. concentrationThe product fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-90de591c052c438e96e669424661f1cd
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323460B2

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