Triethylsilane → [Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester

HRID 479145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479145
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([O:36][CH3:37])[CH:6](O)[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[CH:9][CH:8]=1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:38])[CH:5]([O:36][CH3:37])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[O:24][C:25]=2[CH3:26])=[CH:9][CH:8]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 695567193-Hydroxy-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester

Produkt 1

HCID 69556683[Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl esterAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

0.228 g of the above prepared 3-hydroxy-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester (0.44 mmol) was dissolved in 2.3 ml of trifluoroacetic acid, treated at 0° with 0.697 ml of triethylsilane (10 eq.) and then kept for 4 h at 0°. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed twice with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 0.143 g of the title compound as colorless oil.

Aufarbeitung

  1. additionThe reaction mixture was then poured
  2. washthe organic layer washed twice with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-78f7e8b44396410eb73ff0ada8bebe63
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

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