Sodium Hydroxide → 1-[2-Acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline

HRID 1447637

Reaktionsgleichung

Reaktionsgleichung von HRID 1447637
[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH2:11][CH2:12][NH2:13])[C:7]([OH:9])=O)(=[O:3])[CH3:2].C1C([N+]([O-])=O)=CC=C(O[C:24]([C:26]([F:29])([F:28])[F:27])=[O:25])C=1.[NH:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=[O:33].[OH-].[Na+]>N1C=CC=CC=1.O>[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH2:11][CH2:12][NH:13][C:24](=[O:25])[C:26]([F:27])([F:28])[F:29])[C:7]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=[O:33])=[O:9])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 695694-Nitrophenyl trifluoroacetateHCID 145742L-ProlineHCID 134246592-[(Acetylsulfanyl)methyl]-5-aminopentanoic acid

Produkt 1

HCID 540982051-[2-Acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 2-acetylthiomethyl-5-aminopentanoic acid (2.05 g.) and p-nitrophenyltrifluoroacetate (5.6 g.) in pyridine (10 ml.) is stirred at room temperature for four hours, and then added dropwise to a vigorously stirred solution of L-proline (1.55 g.) in water (10 ml.) while keeping the pH at 9 with careful addition of 2 N sodium hydroxide. When the consumption of sodium hydroxide stops, the reaction mixture is acidified with hydrochloric acid and extracted with ethyl acetate. The solvent is removed in vacuo and the residue is chromatographed on a silica gel column to yield 1-[2-acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline.

Aufarbeitung

  1. customWhen the consumption of sodium hydroxide
  2. extractionextracted with ethyl acetate
  3. customThe solvent is removed in vacuo
  4. customthe residue is chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-093901b511b341b28b69358266cc88b4
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04177277

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