4-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3 methylbutyryl)oxazolidin-2-one → 4-(R)-Benzyl-3-(3-methyl-2-(R)-{4-[5-(4-trifluoromethylphenyl)pyrimidin-2-yl]piperazine-1sulfonylmethyl}butyryl)oxazolidin-2-one

HRID 393733Notes

Reaction equation

HRID 393733 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:42])[C@H:15]([CH2:19][S:20](N1CCN(C2N=CC(C3C=CC(F)=CC=3)=CN=2)CC1)(=[O:22])=[O:21])[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[N:45]1([C:51]2[N:56]=[CH:55][C:54]([C:57]3[CH:62]=[CH:61][C:60]([C:63]([F:66])([F:65])[F:64])=[CH:59][CH:58]=3)=[CH:53][N:52]=2)[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C([C@@H]1COC(=O)N1C(=O)[C@H](CS(Cl)(=O)=O)C(C)C)C1C=CC=CC=1>>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:42])[C@H:15]([CH2:19][S:20]([N:48]1[CH2:49][CH2:50][N:45]([C:51]2[N:52]=[CH:53][C:54]([C:57]3[CH:58]=[CH:59][C:60]([C:63]([F:64])([F:66])[F:65])=[CH:61][CH:62]=3)=[CH:55][N:56]=2)[CH2:46][CH2:47]1)(=[O:22])=[O:21])[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 228882844-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3 methylbutyryl)oxazolidin-2-oneHCID 235197544-(R)-benzyl-3(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl)piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-oneHCID 1317245832-Piperazin-1-yl-5-(4-trifluoromethylphenyl)pyrimidine, dihydrochloride

Product 1

HCID 235197554-(R)-Benzyl-3-(3-methyl-2-(R)-{4-[5-(4-trifluoromethylphenyl)pyrimidin-2-yl]piperazine-1sulfonylmethyl}butyryl)oxazolidin-2-oneYield 86%

Procedure

Prepared according to the method for the preparation of 4-(R)-benzyl-3(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methyl-butyryl)oxazolidin-2-one, from 2-piperazin-1-yl-5-(4-trifluoromethylphenyl)-pyrimidine, dihydrochloride (0.250 g) and 4-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3-methylbutyryl)-oxazolidin-2-one (0.360 g), to yield the title compound as an off-white solid (0.480 g, 86%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0606815a8aa74e82939b185cec0d5d0d
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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