Reaktion #572369

ord-244be213176e4281b3c133665b57ae3d

Reaktionsgleichung

CC(=O)O.CCCCO.O
butanol acetic acid water
C[C@H](NCC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
1-[N-[(S)-3-(Benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, 1,1-dimethylethyl ester
Cl.O=C(O)[C@@H]1CCCN1
L-proline, monohydrochloride
CO
methanol
→
C[C@H](NCC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)O.Cl
1-[N-[(S)-3-(Benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, monohydrochloride

Edukte

CC(=O)O.CCCCO.O
butanol acetic acid water
C[C@H](NCC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
1-[N-[(S)-3-(Benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, 1,1-dimethylethyl ester
Cl.O=C(O)[C@@H]1CCCN1
L-proline, monohydrochloride
CO
methanol

Reagenzien

Keine

Lösungsmittel

Cl
hydrogen chloride
CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenIt is then concentrated
  2. 2
    Filtrationfiltered
  3. 3
    Sonstigeto obtain 600 mg

Vorschrift

1-[N-[(S)-3-(Benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, 1,1-dimethylethyl ester (740 mg., 1.46 mmole) is dissolved in a solution of hydrogen chloride in acetic acid (1.5N, 10 ml.) and kept at room temperature for 30 minutes. It is then concentrated, taken into water, filtered and lyophilized to obtain 600 mg. of 1-[N-(S)-3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, monohydrochloride; m.p. 83°-163°; [α]D25 =-109° (c=1.04, methanol). Rf 0.6 (silica gel; butanol/acetic acid/water, 4:1:1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04535176uspto-grants-1985_08