(5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-one → 5(R)-Isoxazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)oxazolidin-2-one

HRID 723816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723816
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18][CH:17]=3)=[C:11]([F:29])[CH:10]=2)[CH2:4]1.O[C:31]1[CH:35]=[CH:34][O:33][N:32]=1>>[O:33]1[CH:34]=[CH:35][C:31]([O:1][CH2:2][C@@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[C:13]([F:15])[C:12]([C:16]4[CH2:21][CH2:20][N:19]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:18][CH:17]=4)=[C:11]([F:29])[CH:10]=3)[CH2:4]2)=[N:32]1

Komponenten

3

Edukt 2

HCID 11304129(5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-oneHCID 178516613HCID 178516613, Verbindung

Produkt 1

HCID 114768705(R)-Isoxazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)oxazolidin-2-one

Versuchsvorschrift

PCT Application No. GB99/01753 (Publication No. WO 99/64417) describes the preparation of 5(R)-Hydroxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)oxazolidin-2-one (Reference Example 4 of GB99/01753), which is reacted under Mitsunobu conditions with 3-hydroxyisoxazole to give 5(R)-Isoxazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)oxazolidin-2-one (Reference Example 5 of GB99/01753). Purification (by column chromatography) and subsequent reaction with 1-chloroethyl chloroformate and work-up gives 5(R)-Isoxazol-3-yloxymethyl-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)oxazolidin-2-one (Reference Example 6 of GB99/01753).

Quellen und Nachweise

ORD-Eintrag
ord-86411129065b4ed5a516984c8616c3e9
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141583B2

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