Isopropanol → N-[(S)-6-(2-Oxoethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913816
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C@@H:9]([NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][O:25]3)=[CH:18][CH:17]=1)[CH2:8][CH2:7]2)[CH:2]=C.CC([OH:33])C.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[O:33]=[CH:2][CH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C@@H:9]([NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][O:25]3)=[CH:18][CH:17]=1)[CH2:8][CH2:7]2

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 23667635Sodium periodateHCID 67544894N-((S)-6-allyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Produkt 1

HCID 86645828N-[(S)-6-(2-Oxoethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-((S)-6-allyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.50 g), 2-propanol (50 ml) and water (50 ml) was admixed with sodium periodate (0.60 g) and osmium tetroxide (1.3 mg). After stirring vigorously for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The product was thus obtained with the molecular weight of 393.49 (C24H27NO4); MS (ESI): 394 (M+H+).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was thus obtained with the molecular weight of 393.49 (C24H27NO4)

Quellen und Nachweise

ORD-Eintrag
ord-36a631f47e1f48f98ef04a5d17adcd52
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609731B2

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