Benzyl chloroformate → (R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

HRID 737174

Reaktionsgleichung

Reaktionsgleichung von HRID 737174
[S:1]1[CH2:5][C@@H:4]([C:6]([OH:8])=[O:7])[NH:3][CH2:2]1.CCN(C(C)C)C(C)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CN(C=O)C>[CH2:22]([O:21][C:19]([N:3]1[C@H:4]([C:6]([OH:8])=[O:7])[CH2:5][S:1][CH2:2]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 93176L-Thioproline

Produkt 1

HCID 11119045(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(R)-Thiazolidine-4-carboxylic acid (309.9 mg, 2.33 mmol) was dissolved in DMF (10 mL) and distilled water (10 mL). The solution was cooled to 0° C., and DIEA (0.590 mL, 3.39 mmol) was added followed by benzyl chloroformate (0.485 mL, 3.40 mmol). The reaction was stirred at 0° C. and allowed to warm to ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product.

Aufarbeitung

  1. distillationdistilled water (10 mL)
  2. temperatureto warm to ambient temperature overnight
  3. filtrationThe reaction was filtered
  4. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-aa810961bef348658de3df2fc279b3f4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595398B2

Verknüpfte Notizen

Wird geladen…