Hydrochloric Acid → (2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 1065654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1065654
[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(=O)(O)[O-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[C:11]([N:5]1[CH2:6][CH:2]([OH:1])[CH2:3][C@H:4]1[C:7]([OH:9])=[O:8])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 69248L-Proline, 4-hydroxy-, cis-HCID 516893Potassium Bicarbonate

Produkt 1

HCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

26.5 g. (0.02 mole) of 4-hydroxy-L-proline and 32.8 ml. (0.23 mole) of benzyl chloroformate are reacted in 200 ml. of water and 100 ml. of acetone in the presence of 20 g. (0.02 mole) of potassium bicarbonate and 69.2 g. (0.50 mole) of potassium carbonate and worked up with 90 ml. of concentrated hydrochloric acid as described in Can.J. Biochem. & Physiol. 37, 584 (1959) to obtain N-carbobenzyloxy-4-hydroxy-L-proline. This product is reacted with cyclohexylamine to form the cyclohexylamine salt yield 69 g., m.p. 193°-195°. The salt (34 g.) is neutralized with N-hydrochloric acid to obtain 27 g. of free acid as a colorless glass [α]D26 -70°, (c, 1% in chloroform).

Quellen und Nachweise

ORD-Eintrag
ord-0f9b8529a9d845afab6d953ea54f3e22
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04330548

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