Toluene → Benzyloxycarbonyl-L-proline

HRID 21765

Reaktionsgleichung

Reaktionsgleichung von HRID 21765
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Cl[C:10]([O:12]C1C=CC=CC=1)=[O:11].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[OH-].[Na+]>[C:10]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])([O:12][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:11]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 15891Phenyl chloroformateHCID 145742L-Proline

Produkt 1

HCID 101987Benzyloxycarbonyl-L-prolineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

L-Proline (10 g, 86.6 mmol) was dissolved in 66 mL of 2N NaOH and cooled to 0° C. To this solution were slowly and simultaneously added 34.35 mL of a solution of phenyl chloroformate in toluene (104.2 mmol) and 33 mL of 4N NaOH, over a period of 1 hr, while maintaining the reaction temperature at 0° C. and the pH above 7. After all reactants were added, the reaction was stirred for 6 hr at room temperature. The solution was then extracted with ether. The remaining aqueous layer was neutralized to pH 6-7 with 1N HCl, then extracted with ethyl acetate. The extract was dried over Na2SO4 and concentrated to afford 21.19 g of the title product (98% yield). 1H NMR (CDCl3) δ 9.55 (d, 1H), 7.3 (s, 5H), 5.25 (d, 2H), 4.35 (t, 1H), 4.20 (t, 1H), 1.8-2.2 (m, 4H).

Aufarbeitung

  1. temperaturewhile maintaining the reaction temperature at 0° C.
  2. additionAfter all reactants were added
  3. extractionThe solution was then extracted with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c176d87d6c3c4a96ab95c902ab9d98fb
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424444

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