5-(4-Fluorophenyl)-2-(piperidin-4-yloxy)pyridine → 4-(R)-Benzyl-3-(2-(R)-{4-[5-(4-fluorophenyl)pyridin-2-yloxy]piperidine-1-sulfonylmethyl}-3-methylbutyryl)-oxazolidin-2-one

HRID 393718Notes

Reaction equation

HRID 393718 reaction equation
C(OC(=O)C(CS(N1CCN(C2C=CC(Br)=CC=2)CC1)(=O)=O)C(C)C)(C)(C)C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)=[N:40][CH:41]=2)=[CH:32][CH:31]=1.[CH2:49]([C@@H:56]1[CH2:60][O:59][C:58](=[O:61])[N:57]1[C:62](=[O:72])[C@H:63]([CH2:67][S:68](Cl)(=[O:70])=[O:69])[CH:64]([CH3:66])[CH3:65])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH2:49]([C@@H:56]1[CH2:60][O:59][C:58](=[O:61])[N:57]1[C:62](=[O:72])[C@H:63]([CH2:67][S:68]([N:46]1[CH2:47][CH2:48][CH:43]([O:42][C:39]2[CH:38]=[CH:37][C:36]([C:33]3[CH:32]=[CH:31][C:30]([F:29])=[CH:35][CH:34]=3)=[CH:41][N:40]=2)[CH2:44][CH2:45]1)(=[O:70])=[O:69])[CH:64]([CH3:66])[CH3:65])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

4

Reactant 3

HCID 226467305-(4-Fluorophenyl)-2-(piperidin-4-yloxy)pyridineHCID 228882844-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3 methylbutyryl)oxazolidin-2-oneHCID 698952502-[4-(4-Bromo-phenyl)piperazine-1-sulfonylmethyl]3-methylbutyric acid tert-butyl ester

Product 1

HCID 235197524-(R)-Benzyl-3-(2-(R)-{4-[5-(4-fluorophenyl)pyridin-2-yloxy]piperidine-1-sulfonylmethyl}-3-methylbutyryl)-oxazolidin-2-oneYield 75.3%

Procedure

Prepared according to the method for the preparation of 2-[4-(4-bromophenyl)-piperazine-1-sulfonylmethyl]-3-methyl-butyric acid tert-butyl ester, from 5-(4-fluorophenyl)-2-(piperidin-4-yloxy)pyridine (0.52 g) and 4-(R)-Benzyl-3-(2-(R)-chlorosulfonylmethyl-3-methylbutyryl)oxazolidin-2-one (0.57 g) to yield the title compound as an off-white solid (0.70 g, 58%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9c1f27676d1449e88bc6ed71d166cd1e
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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