3(S)-(Benzofuran-6-yl)-3-[benzyl-(1(R)-phenyl-ethyl)-amino]-propionic acid ethyl ester → 3(S)-Amino-3-(2,3-dihydro-benzofuran-6-yl)-propionic acid ethyl ester

HRID 1108391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108391
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@@H:6]([C:23]1[CH:31]=[CH:30][C:26]2[CH:27]=[CH:28][O:29][C:25]=2[CH:24]=1)[N:7](CC1C=CC=CC=1)[C@@H](C1C=CC=CC=1)C)[CH3:2]>CCO.O.CC(O)=O>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@H:6]([NH2:7])[C:23]1[CH:31]=[CH:30][C:26]2[CH2:27][CH2:28][O:29][C:25]=2[CH:24]=1)[CH3:2]

Komponenten

3

Edukt 1

HCID 154537673(S)-(Benzofuran-6-yl)-3-[benzyl-(1(R)-phenyl-ethyl)-amino]-propionic acid ethyl ester

Produkt 1

HCID 108236463(S)-Amino-3-(2,3-dihydro-benzofuran-6-yl)-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86584229Acetic acid ethanol waterLösungsmittel

Versuchsvorschrift

A mixture of the dibenzylamine 3-5 (1.19 g, 2.78 mmol) in EtOH/H2O/AcOH (26 mL/3 mL/1.0 mL) was degassed with argon and treated with Pd(OH)2 (1.19 g). The mixture was placed under 1 atm of H2. After stirring for 18 h, the mixture was diluted with EtOAc, and filtered through celite. The filtrate was concentrated and the residue purified by flash chromatography (10% ethyl acetate/dichloromethane) to give the ester 3-6 as a white solid.

Aufarbeitung

  1. customwas degassed with argon
  2. additiontreated with Pd(OH)2 (1.19 g)
  3. additionthe mixture was diluted with EtOAc
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by flash chromatography (10% ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-04f47ce171894a2285ae9e307713c970
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066648

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