(+)-Styrene oxide → methyl 4'-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

HRID 2220378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220378
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([NH:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]1[O:39][C@@H:32]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[CH2:1]([N:8]([CH2:31][C@H:32]([OH:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([NH:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 114705(+)-Styrene oxideHCID 69103631Methyl 4'-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

Produkt 1

HCID 69103734methyl 4'-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4′-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (250 mg) in ethanol (15 ml) was added (R)-(+)-styreneoxide (142 μl) at room temperature, and the mixture was stirred under reflux for 48 hours. The mixture was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (251 mg).

Aufarbeitung

  1. temperatureunder reflux for 48 hours
  2. customThe mixture was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-8781383c3f4643a6adfc9e8ea92acf1e
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417060B2

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