(4S)-4-(Benzoyloxymethyl)oxazolidine-2-one → benzoic acid (R)-3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}-2-oxooxazolidin-4-ylmethyl ester

HRID 1803963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803963
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:3]=1.[O:29]=[C:30]1[NH:34][C@H:33]([CH2:35][O:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:32][O:31]1>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:34]4[C@H:33]([CH2:35][O:36][C:37](=[O:44])[C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH2:32][O:31][C:30]4=[O:29])=[CH:3][C:4]=3[S:25]([CH3:28])(=[O:27])=[O:26])=[O:9])[CH2:11][CH2:12]2)=[O:24])=[CH:18][CH:19]=1

Komponenten

3

Edukt 2

HCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 67380967(4-Bromo-2-methanesulfonylphenyl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone

Produkt 1

HCID 54755002benzoic acid (R)-3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]-3-methanesulfonylphenyl}-2-oxooxazolidin-4-ylmethyl esterAusbeute 48,5 %

Versuchsvorschrift

By reaction and treatment in the same manner as in Preparation Example 1 and using 4-bromo-2-methylsulfonylbenzoic acid (2.8 g) and (4-chlorophenyl)piperidin-4-ylmethanone (2.6 g), (4-bromo-2-methanesulfonylphenyl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone (4.8 g) was obtained. By reaction and treatment in the same manner as in Preparation Example 12 and using (4-bromo-2-methanesulfonylphenyl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone (1.5 g) and benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (796 mg), the title compound (938 mg) was obtained.

Aufarbeitung

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 12

Quellen und Nachweise

ORD-Eintrag
ord-c9359ff7f8414afd82b5a0102351dfda
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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