Tetrahydrofuran → Ethyl 2-amino-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

HRID 356315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356315
[N:1]([CH:4]([CH:10]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[NH2:1][CH:4]([CH:10]([O:18][Si:19]([C:22]([CH3:23])([CH3:25])[CH3:24])([CH3:21])[CH3:20])[C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 23298343Ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

Produkt 1

HCID 23298326Ethyl 2-amino-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionateAusbeute 113 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5.6 g of ethyl 2-azido-3-t-butyl-dimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate (prepared as described in Preparation 77), 7.5 g of triphenylphosphine and 18 ml of a 8:1 by volume mixture of tetrahydrofuran and water was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate and subsequently a 50:1 by volume mixture of methylene chloride and methanol as the eluent, to give 5.9 g of the title compound having Rf=0.59 (on silica gel thin layer chromatography using a 15:1 by volume mixture of methylene chloride and methanol as the developing solvent).

Aufarbeitung

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation
  2. customThe residue was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate
  4. additionsubsequently a 50:1 by volume mixture of methylene chloride and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-af57051003bb4beaa158164e150a841a
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834501

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