Water → HCID 68683629, Verbindung

HRID 1713801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713801
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].Cl.[O:9]([CH2:16][CH2:17][CH2:18][NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1.O>C(Cl)Cl>[O:7]=[C:2]([NH:19][CH2:18][CH2:17][CH2:16][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 18590545(3-Aminopropoxy)benzene hydrochloride

Produkt 1

HCID 68683629HCID 68683629, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl chloro(oxo)acetate (1.77 mL) was added to a stirred solution of (3-phenoxypropyl)amine hydrochloride (3000 mg) and pyridine (2.98 mL) in DCM (100 mL) at 0° C. After the addition was complete the solution was allowed to warm to ambient temperature and stirred for 16 hours. Water (50 mL) was added and the mixture was extracted with DCM (2×75 mL). The organic extracts were combined, washed with brine (50 mL), dried and concentrated in vacuo to give an oil. This was purified by flash chromatography on a 90 g Biotage™ silica column using a gradient of 10-60% EtOAc in hexane as the eluent to give methyl oxo[(3-phenoxypropyl)amino]acetate (3212 mg) as a solid; 1H NMR δ (CDCl3) 7.60 (1H, bs), 7.28 (2H+CHCl3, m), 6.94 (3H, m), 4.07 (2H, t), 3.90 (3H, s), 3.58 (2H, quartet), 2.08 (2H, m), +0.1 mole of EtOAc; MS m/e MH+ 238.

Aufarbeitung

  1. additionAfter the addition
  2. extractionthe mixture was extracted with DCM (2×75 mL)
  3. washwashed with brine (50 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on a 90 g Biotage™ silica column

Quellen und Nachweise

ORD-Eintrag
ord-a662f939efc54032a8cc040008ab7831
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795283B2

Notizen zur Reaktion

Wird geladen…