Triphenylphosphine → Methyl 3-{4-[(tert-butoxycarbonyl)amino]butoxy}-1-(methoxymethoxy)-2-naphthoate

HRID 488681

Reaktionsgleichung

Reaktionsgleichung von HRID 488681
[OH:1][C:2]1[C:3]([C:16]([O:18][CH3:19])=[O:17])=[C:4]([O:12][CH2:13][O:14][CH3:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:39]([O:43][C:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50]O)=[O:45])([CH3:42])([CH3:41])[CH3:40].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:39]([O:43][C:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][O:1][C:2]1[C:3]([C:16]([O:18][CH3:19])=[O:17])=[C:4]([O:12][CH2:13][O:14][CH3:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:45])([CH3:42])([CH3:41])[CH3:40]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 22271918HCID 22271918, Verbindung

Produkt 1

HCID 22271972Methyl 3-{4-[(tert-butoxycarbonyl)amino]butoxy}-1-(methoxymethoxy)-2-naphthoateAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of methyl 3-hydroxy-1-(methoxymethoxy)-2-naphthoate (41 mg, 0.16 mmol), triphenylphosphine (41 mg, 0.16 mmol) and N-(tert-butoxycarbonyl)-4-hydroxy-1-butylamine (33 mg, 0.17 mmol) in THF (0.5 mL) was added diethylazodicarboxylate (30 μL, 0.19 mmol). The mixture was stirred at ambient temperature for 30 minutes, concentrated under reduced pressure and purified on silica gel eluting with 30% ethyl acetate/hexanes to provide the titled compound (28 mg, 41%).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. custompurified on silica gel eluting with 30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2255b90bb88b40b8aaf957c537c5f008
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972340B2

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