(-)-N-[1-(R)-Ethoxycarbonxyl-3-phenylpropyl]-L-alanine → N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

HRID 1953817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953817
[CH2:1]([O:3][C:4]([C@H:6]([NH:15][C@H:16]([C:18]([OH:20])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].C(OC(C(N[C@H](C(O)=O)C)CCC1CCCCC1)=O)C.C(C(N[C@H](C(O)=O)C)CCC1C=CC=CC=1)(O)=O>>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([OH:20])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 3

HCID 7157261(-)-N-[1-(R)-Ethoxycarbonxyl-3-phenylpropyl]-L-alanineHCID 21971197N-(1-carboxy-3-phenylpropyl)-L-alanineHCID 54322184N-(1-ethoxycarbonyl-3-cyclohexylpropyl)-L-alanine

Produkt 1

HCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanineAusbeute 85 %

Versuchsvorschrift

According to the same manner as that described in Example 1, the catalytic reduction was carried out to give a reaction solution containing 10% (w/w) of N-(1(R)-ethoxycarbonyl-3-phenylpropyl)-L-alanine, 0.1% (w/w) of N-(1-ethoxycarbonyl-3-cyclohexylpropyl)-L-alanine and 7% (w/w) of N-(1-carboxy-3-phenylpropyl)-L-alanine, based on N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine, respectively. The reaction yield was 85%. According to the same manner as that described in Example 1, the crystallization from the reaction solution was carried out to give N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine (6.3 g, 23 mmoles). The yield from N-(1(S)-ethoxycarbonyl-3-oxo-3-phenylpropyl)-L-alanine: 75%, HPLC purity: 99.0% (w/w), the content of N-(1(R)-ethoxycarbonyl-3-phenylpropyl)-L-alanine: not detected, the content of N-(1-ethoxycarbonyl-3-cyclohexylpropyl)-L-alanine: 0.1% (w/w), the content of N-(1-carboxy-3-phenylpropyl)-L-alanine: 0.1% (w/w), residue on ignition: 0.1% (w/w).

Aufarbeitung

  1. customto give a reaction solution
  2. customThe reaction yield was 85%
  3. customthe crystallization from the reaction solution

Quellen und Nachweise

ORD-Eintrag
ord-7ece5419f9104871971e7f7480b2192b
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06118010

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