Hydrogen Bromide → 4-keto-L-proline hydrobromide

HRID 848447

Reaktionsgleichung

Reaktionsgleichung von HRID 848447
C([N:11]1[CH2:18][C:17](=[O:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[BrH:20]>C(O)(=O)C>[BrH:20].[O:19]=[C:17]1[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 11076282N-Carbobenzyloxy-4-keto-L-proline

Produkt 1

HCID 127736614-keto-L-proline hydrobromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 4.0 g. (0.015 mole) of N-carbobenzyloxy-4-keto-L-proline are added 20 ml. of hydrogen bromide in acetic acid (30-32%). The mixture is frequently swirled over a period of eight minutes. At the end of this period (effervescence has stopped), the yellow-orange solution is layered over with 250 ml. of ether, triturating the gummy product. The ether is discarded and the resulting tacky solid is triturated with fresh ether and finally with 50 ml. of acetonitrile to give 4-keto-L-proline, hydrobromide as a crystalline solid weighing 2.7 g. (85%), m.p. 153°-155° (dec.,), [α]D26 -49° (c, 1% in water).

Aufarbeitung

  1. customof ether, triturating the gummy product
  2. customthe resulting tacky solid is triturated with fresh ether and finally with 50 ml

Quellen und Nachweise

ORD-Eintrag
ord-65f5391bedc94b09bc9e382f5da62b09
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04296113

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