Triphenylphosphine → (R)-tert-butyl 4-((1R,2S)-3-azido-1-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 924425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924425
C1C=CC(OP(OC2C=CC=CC=2)([N:10]=[N+:11]=[N-:12])=O)=CC=1.[Si:20]([O:27][C@@H:28]([C@H:33]1[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[N:34]1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:29]([CH3:32])[CH2:30]O)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[N:10]([CH2:30][C@H:29]([CH3:32])[C@H:28]([C@H:33]1[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[N:34]1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[O:27][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[N+:11]=[N-:12]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 123414Diphenylphosphoryl azideHCID 59226545(R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 59226479(R)-tert-butyl 4-((1R,2S)-3-azido-1-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diphenylphosphonic azide (1.3 mL, 5.9 mmol) was added to a mixture of tert-butyl (4R)-4-((1R,2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2-methylpropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.2 g, 3.0 mmol), diisopropyl azodicarboxylate (1.2 mL, 5.9 mmol) and PPh3 (1.6 g, 5.9 mmol) in THF (20 mL). The mixture was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with 0-15% EtOAc in hexanes) to provide the sub-title compound (1.09 g, 86%). LCMS calc. for C15H33N4O2Si (M+H-Boc)+: m/z=329.2. found 329.2.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel (eluting with 0-15% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-643c7aa088d5407bb42324435f93d37f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278950B2

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