Water → Methyl (2E)-3-{2-[(1R)-1-{[(2R)-3-[[1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-yl]amino}-2-hydroxypropyl]oxy}ethyl]phenyl}prop-2-enoate

HRID 1927292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927292
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])[CH3:7].[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH:21]1[CH2:29][C:30]([CH3:33])([NH2:32])[CH3:31].Cl([O-])(=O)(=O)=O.[Li+].O>C1(C)C=CC=CC=1>[CH2:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH:21]1[CH2:29][C:30]([NH:32][CH2:3][C@@H:2]([OH:1])[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])[CH3:7])([CH3:31])[CH3:33]

Komponenten

6

Edukt 4

HCID 962WaterHCID 98341731-(2,3-Dihydro-1H-inden-2-yl)-2-methylpropan-2-amineHCID 23665649Lithium perchlorateHCID 58662611methyl (2E)-3-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)prop-2-enoate

Produkt 1

HCID 58572784Methyl (2E)-3-{2-[(1R)-1-{[(2R)-3-[[1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-yl]amino}-2-hydroxypropyl]oxy}ethyl]phenyl}prop-2-enoateAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of methyl (2E)-3-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)prop-2-enoate (342 mg, 1.30 mmol) described in WO 2004/106280, 1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-amine (234 mg, 1.24 mmol) described in WO 01/53254, and lithium perchlorate (79 mg, 0.74 mmol) in toluene (12 mL) was stirred at room temperature for 16 hours. Water (10 mL) was added to the reaction solution, which was then extracted with ethyl acetate (10 mL×3). After that, the organic layers were combined, washed with saturated brine, and washed with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound as a colorless oily substance (206 mg, yield 37%).

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate (10 mL×3)
  2. washwashed with saturated brine
  3. washwashed with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9aa67c9962274f48a0f8847a81e463d6
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183272B2

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