Sodium Hydroxide → N-(1-Methoxycarbonyl-3-methylthiopropyl)-alanyl-L-proline

HRID 2418413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2418413
[C:1]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])(=[O:5])[C:2]([CH3:4])=O.[CH3:14][O:15][C:16](=[O:23])[C@H:17]([CH2:19][CH2:20][S:21][CH3:22])[NH2:18].C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH3:14][O:15][C:16]([CH:17]([NH:18][C@H:2]([C:1]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:4])[CH2:19][CH2:20][S:21][CH3:22])=[O:23]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 5003444Sodium cyanoborohydrideHCID 10130260(S)-1-(2-Oxopropanoyl)pyrrolidine-2-carboxylic acid

Produkt 1

HCID 54124052N-(1-Methoxycarbonyl-3-methylthiopropyl)-alanyl-L-prolineAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of pyruvoyl-L-proline (185 mg), L-methionine methyl ester (600 mg), and sodium cyanoborohydride (200 mg) in 20 ml of methanol is adjusted to neutrality with dilute methanolic sodium hydroxide. After standing at room temperature for three days the product is absorbed on strong acid ion-exchange resin and eluted with 2% pyridine in water to yield 80 mg of product. The nmr spectrum shows OCH3 at 3.95δ, S-CH3 at 2.2δ and CH-CH3 at 1.55 and 1.7δ. The mass spectrogram on silylated material shows the expected molecular ion at 404 m/e.

Aufarbeitung

  1. customthe product is absorbed on strong acid ion-exchange resin
  2. washeluted with 2% pyridine in water

Quellen und Nachweise

ORD-Eintrag
ord-435595efafa6448d80650cb0b7533bb6
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04472380

Notizen zur Reaktion

Wird geladen…