Water → benzyl 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylate

HRID 30765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30765
CS(O[CH2:6][CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:32])(=O)=O.[NH2:33][C@@H:34]([CH3:44])[C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[OH:36].C(NC(C)C)(C)C.O>CN(C)C=O.C(OCC)(=O)C>[OH:36][C@H:35]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[C@@H:34]([NH:33][CH2:6][CH2:7][O:8][C:9]1[C:10]([CH3:32])=[CH:11][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[CH:18][CH:17]=2)=[CH:13][C:14]=1[CH3:15])[CH3:44]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7912DiisopropylamineHCID 6931143P-HydroxynorephedrineHCID 23090786Benzyl 4'-(2-methanesulfonyloxy-ethoxy)-3'5'-dimethylbiphenyl-4-carboxylate

Produkt 1

HCID 68544588benzyl 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylateAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of benzyl 4′-(2-methanesulfonyloxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate (0.20 g), 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (0.074 g) and diisopropylamine (0.074 mL) in N,N-dimethylformamide (2 mL) was stirred at 80° C. overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:methylene chloride/methanol=15/1-10/1) to afford benzyl 4′-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3′,5′-dimethylbiphenyl-4-carboxylate (0.108 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent:methylene chloride/methanol=15/1-10/1)

Quellen und Nachweise

ORD-Eintrag
ord-4337ca67dcbd4891a18f75be4079c9af
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423185B2

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