Hydrochloric Acid → HCID 15117338, Verbindung

HRID 1029679

Reaktionsgleichung

Reaktionsgleichung von HRID 1029679
[S:1]1[CH2:5][C@@H:4]([C:6]([OH:8])=[O:7])[NH:3][CH2:2]1.[N+:9]([C:12]1[CH:22]=[CH:21][C:15]([CH2:16][O:17][C:18](Cl)=[O:19])=[CH:14][CH:13]=1)([O-:11])=[O:10].[OH-].[Na+].Cl>O.O1CCCC1>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]([N:3]2[C@H:4]([C:6]([OH:8])=[O:7])[CH2:5][S:1][CH2:2]2)=[O:19])=[CH:21][CH:22]=1)([O-:11])=[O:10]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 782054-Nitrobenzyl chloroformateHCID 93176L-Thioproline

Produkt 1

HCID 15117338HCID 15117338, VerbindungAusbeute 116,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (R)-thiazolidine-4-carboxylic acid (20.0 g) in a mixture of water (100 ml) and tetrahydrofuran (100 ml) was added a solution of 4-nitrobenzyloxycarbonyl chloride (32.4 g) in tetrahydrofuran (60 ml) under ice-cooling with stirring, keeping the pH between 8.5 and 9.0 with 4N aqueous sodium hydroxide. After stirring for 30 minutes, the mixture was adjusted to pH 1 with concentrated hydrochloric acid, extracted with ethyl acetate, dried over magnesium sulfate, and evaporated under reduced pressure to give (R)-3-(4-nitrobenzyloxycarbonyl)thiazolidine-4-carboxylic acid (54.5 g) as a crude syrup.

Aufarbeitung

  1. temperaturecooling
  2. stirringAfter stirring for 30 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cc4ae1bccec54ac08a1c7fc58fc97212
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102877

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