Tetrahydrofuran → N-Cbz-D-serine-2,2,5-trimethylcyclopentyl ester

HRID 2232689

Reaktionsgleichung

Reaktionsgleichung von HRID 2232689
[C:1]([NH:11][C@@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1COCC1.[CH3:23][C:24]1([CH3:31])[CH2:28][CH2:27][CH:26]([CH3:29])[CH:25]1O>>[CH3:23][C:24]1([CH3:31])[CH2:28][CH2:27][CH:26]([CH3:29])[CH:25]1[O:16][C:15](=[O:17])[C@@H:12]([CH2:13][OH:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 489184Z-D-Ser-OHHCID 212439422,2,5-Trimethylcyclopentanol

Produkt 1

HCID 22839478N-Cbz-D-serine-2,2,5-trimethylcyclopentyl ester

Versuchsvorschrift

Into a suspension of N-Cbz-D-serine (5 g) in 50 ml of dry THF containing 1 equivalent of 2,2,5-trimethylcyclopentanol is bubbled dry hydrogen chloride gas at room temperature. Upon complete solution of the mixture, the reaction is refluxed for 5 hours, then concentrated. Ethyl acetate is added, and this is washed with saturated sodium bicarbonate, water, and dried over MgSO4. Filtration followed by concentration yields N-Cbz-D-serine-2,2,5-trimethylcyclopentyl ester. 5 g of this product is dissolved in 10 ml methanol and hydrogenated in a Paar apparatus over 1 g of 5% Pd/C to yield 2,2,5-trimethylcyclopentyl-D-serinate.

Aufarbeitung

  1. customis bubbled dry hydrogen chloride gas at room temperature
  2. temperatureUpon complete solution of the mixture, the reaction is refluxed for 5 hours
  3. concentrationconcentrated
  4. additionEthyl acetate is added
  5. washthis is washed with saturated sodium bicarbonate, water
  6. dry with materialdried over MgSO4
  7. filtrationFiltration
  8. concentrationfollowed by concentration

Quellen und Nachweise

ORD-Eintrag
ord-534ac3e1eb594089be47259796c39af6
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788332

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