Triphenylphosphine → HCID 86749470, Verbindung

HRID 439412

Reaktionsgleichung

[C:1]([NH:8][CH2:9][CH:10](O)[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1([O:38][C:39]([NH:41][O:42][C:43]([O:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:44])=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:32]1([O:38][C:39]([N:41]([CH:10]([CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH3:11])[O:42][C:43]([O:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:44])=[O:40])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A one liter roundbottom flask was charged with N-Boc-1-amino-2-propanol (26.42 g, 0.0151 mol), triphenylphosphine (41.4 g, 0.158 mol), and N,O-bisphenyloxycarbonylhydroxylamine (43.2 g, 0.158 mol), and dry THF (550 mL). The solution was cooled to 0° C., and diethylazodicarboxylate (24.9 mL, 0.158 mol) was added in THF (50 mL). The reaction was stirred one hour after removing the cooling bath, and concentrated under vacuum. Chromatographic purification is enhanced by adding dichloromethane (200 mL) and concentrating in vacuo twice to remove THF before column chromatography (400 g silica gel, 15% EtOAc/Hex) to provide N,O-bisphenyloxycarbonyl-t-butyloxycarbonylamino-2-propylhydroxylamine (54.4 g, 80%).

Aufarbeitung

customafter removing the cooling bath
concentrationconcentrated under vacuum
customChromatographic purification
additionby adding dichloromethane (200 mL)
concentrationconcentrating in vacuo twice
customto remove THF before column chromatography (400 g silica gel, 15% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag: ord-fc2cceba9ecc4dca8fefd09f509b12a8
Quelldatensatz: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05514702

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