Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acid → HCID 69556452, Verbindung

HRID 479239

Reaktionsgleichung

Reaktionsgleichung von HRID 479239
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:25])[C:9]=1[O:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18])[CH:5]=[O:6].[CH2:26]([C@H:33]1[CH2:37][O:36][C:35](=[O:38])[N:34]1[C:39](=[O:44])[CH2:40][O:41][CH2:42][CH3:43])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.B(OS(C(F)(F)F)(=O)=O)(CCCC)CCCC>>[CH2:26]([C@H:33]1[CH2:37][O:36][C:35](=[O:38])[N:34]1[C:39](=[O:44])[C@@H:40]([O:41][CH2:42][CH3:43])[C@@H:5]([C:4]1[CH:3]=[C:2]([CH3:1])[C:9]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])=[C:8]([CH3:25])[CH:7]=1)[OH:6])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

4

Edukt 3

HCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-oneHCID 180036043,5-Dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

Produkt 1

HCID 69556452HCID 69556452, Verbindung

Versuchsvorschrift

In analogy to the procedures described in examples 11 a] to 11 c], 3,5-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde (example 117) was reacted with (S)-4-benzyl-3-ethoxyacetyl-oxazolidin-2-one and nBu2BOTf to yield (S)-4-benzyl-3-((2S,3R)-3-{3,5-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-ethoxy-3-hydroxy-propionyl)-oxazolidin-2-one (according to NMR, one of the four isomers is strongly predominating; the configuration was tentatively assigned as 2S, 3R according to Tetrahedron Asymmetry 1999, 1353). Reduction of (S)-4-benzyl-3-((2S,3R)-3-}3,5-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-ethoxy-3-hydroxy-propionyl)-oxazolidin-2-one with triethylsilane in trifluoroacetic acid then gave (S)-4-benzyl-3-((2S)-3-{3,5-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-ethoxy-propionyl)-oxazolidin-2-one. The (S)-4-benzyl-3-((2S)-3-{3,5-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-ethoxy-propionyl)-oxazolidin-2-one was subsequently saponified with 1N NaOH in THF to yield (2S)-3-{3,5-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-ethoxy-propionic acid as colorless solid. The enantiomeric excess was judged according to chiral HPLC (Chiralpak-AD) to be 98.8%.

Quellen und Nachweise

ORD-Eintrag
ord-8c79ab243030458ca7d362771f2ba34a
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

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