L-Proline, ethyl ester → HCID 131716003, Verbindung

HRID 231942

Reaktionsgleichung

Reaktionsgleichung von HRID 231942
[F:1][C:2]([F:45])([F:44])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]([O:23][P:24]([CH:28]([NH:33]C(OCC1C=CC=CC=1)=O)[CH2:29][CH2:30][CH2:31][CH3:32])([O:26][CH3:27])=[O:25])[C:11]([N:13]1[CH2:22][CH2:21][CH2:20][C@H:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12])=[O:4].N1CCC[C@H]1C(OCC)=O>CO.[OH-].[OH-].[Pd+2]>[F:44][C:2]([F:1])([F:45])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]([O:23][P:24]([CH:28]([NH2:33])[CH2:29][CH2:30][CH2:31][CH3:32])([O:26][CH3:27])=[O:25])[C:11]([N:13]1[CH2:22][CH2:21][CH2:20][C@H:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12])=[O:4]

Komponenten

5

Edukt 2

HCID 79888L-Proline, ethyl esterHCID 1317160041-[(S)-6-[(Trifluoroacetyl)amino]-2-[[[1-[[(phenylmethoxy)carbonyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxohexyl]-L-proline, ethyl ester

Produkt 1

HCID 131716003HCID 131716003, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The ethyl ester product from part (e) (1.75 g., 2.63 mmole) is dissolved in methanol (75 ml.) at room temperature under argon. The solution is hydrogenated with 20% palladium hydroxide on carbon catalyst (300 mg.) at room temperature and atmospheric pressure for 3 hours. The reaction is filtered through Celite to remove the catalyst, and the volatiles are evaporated to give 1.7 g. of 1-(S)-6-[(Trifluoroacetyl)amino]-2-[[[(1-amino)pentyl]methoxyphosphinyl]oxy]-1-oxohexyl]-L-proline, ethyl ester.

Aufarbeitung

  1. filtrationThe reaction is filtered through Celite
  2. customto remove the catalyst
  3. customthe volatiles are evaporated
  4. customto give 1.7 g

Quellen und Nachweise

ORD-Eintrag
ord-27c87647c46d4e8fbbafb6437f0685fc
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849414

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