Hydrochloric Acid → HCID 68503992, Verbindung

HRID 1176212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176212
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[CH:13]=[C:14]([CH:50]=[CH:51][C:52]=1[OH:53])[CH2:15][O:16][CH:17]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])=[CH:25][CH:24]=2)[CH2:21][CH2:20][N:19]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:18]1.C(=O)([O-])O.[Na+].[OH-].[Na+].Cl>CO.O>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][O:33][CH2:32][CH2:31][CH2:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C@H:22]2[CH2:21][CH2:20][N:19]([C:43]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[O:44])[CH2:18][C@@H:17]2[O:16][CH2:15][C:14]2[CH:50]=[CH:51][C:52]3[O:53][C:2](=[O:3])[NH:11][C:12]=3[CH:13]=2)=[CH:24][CH:25]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 68501582HCID 68501582, Verbindung

Produkt 1

HCID 68503992HCID 68503992, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

0.133 ml of phenyl chloroformate are added dropwise to the stirred emulsion of 0.640 g of tert-butyl 3-(3-amino-4-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.086 g of sodium hydrogencarbonate in 4 ml of methanol and 4 ml of water. The reaction mixture is stirred over 15 minutes and then admixed with 2 ml of methanol. After a further 15 minutes, it is admixed with 0.51 ml of 2N NaOH. After a further 10 minutes, the mixture is admixed with 20 ml of 0.5N HCl and extracted with tert-butyl methyl ether (2×30 ml). The organic phases are washed successively with water (30 ml) and brine (30 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.52 (3:1 EtOAc-heptane); Rt=5.56.

Aufarbeitung

  1. waitAfter a further 15 minutes
  2. waitAfter a further 10 minutes
  3. extractionextracted with tert-butyl methyl ether (2×30 ml)
  4. washThe organic phases are washed successively with water (30 ml) and brine (30 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-ee33e452836f4170b426fa52dc31da3d
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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