Triphenylphosphine → 3-(4-Amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-n-methyl-succinamic acid tert-butyl ester

HRID 1814314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814314
[N:1]1[C:10]2[C:5](=[C:6]([CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]([O:37][C:38](=[O:57])[CH2:39][CH:40]([NH:45][S:46]([C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][C:50]=1O)(=[O:48])=[O:47])[C:41]([NH:43][CH3:44])=[O:42])([CH3:36])([CH3:35])[CH3:34].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:33]([O:37][C:38](=[O:57])[CH2:39][CH:40]([NH:45][S:46]([C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][C:50]=1[O:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)(=[O:48])=[O:47])[C:41]([NH:43][CH3:44])=[O:42])([CH3:36])([CH3:34])[CH3:35]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 696924193-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester

Produkt 1

HCID 696922433-(4-Amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-n-methyl-succinamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 0.167 g (0.972 mmol) 2-quinolin-5-yl-ethanol, 0.48 g (1.94 mmol) triphenyl phosphine, and 0.392 g (0.972 mmol) 3-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester was stirred in 25 mL THF at room temperature under a nitrogen atmosphere. 0.31 mL (1.94 mmol) diethyl azodicarboxylate was added dropwise and the mixture stirred 18 h. TLC anaylsis indicated complete reaction. The solvent was evaporated under reduced pressure and the residue purified on silica eluting with 1:1 hexanes:EtOAc to EtOAc yielding 0.23 g (43%) of 3-(4-amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester as a colorless foam. MS (APCI) m/z 559 (M+1).

Aufarbeitung

  1. customTLC anaylsis indicated complete reaction
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue purified on silica eluting with 1:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7ae9f339d610400a9c014147c27df4cb
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875765B2

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