2-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid → 2-(R)-{4-[5-(4-Chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid

HRID 393710Notes

Reaction equation

HRID 393710 reaction equation
FC1C=CC(C2C=NC(N3CCN(S(C[C@H](C(C)C)[C:25]([OH:27])=[O:26])(=O)=O)CC3)=NC=2)=CC=1.C([C@@H]1COC(=O)N1C(=O)[C@H:45]([CH2:49][S:50]([N:53]1[CH2:58][CH2:57][N:56]([C:59]2[CH:64]=[CH:63][C:62]([C:65]3[CH:70]=[CH:69][C:68]([Cl:71])=[CH:67][CH:66]=3)=[CH:61][N:60]=2)[CH2:55][CH2:54]1)(=[O:52])=[O:51])[CH:46]([CH3:48])[CH3:47])C1C=CC=CC=1>>[Cl:71][C:68]1[CH:69]=[CH:70][C:65]([C:62]2[CH:63]=[CH:64][C:59]([N:56]3[CH2:55][CH2:54][N:53]([S:50]([CH2:49][C@H:45]([CH:46]([CH3:47])[CH3:48])[C:25]([OH:27])=[O:26])(=[O:51])=[O:52])[CH2:58][CH2:57]3)=[N:60][CH:61]=2)=[CH:66][CH:67]=1

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197504-(R)-Benzyl-3-(2-(R)-{4-[5-(4-chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyryl)-oxazolidin-2-one

Product 1

HCID 235197362-(R)-{4-[5-(4-Chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidYield 33%

Procedure

Prepared according to the method for the preparation of 2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid, from 4-(R)-benzyl-3-(2-(R)-{4-[5-(4-chlorophenyl)pyridin-2-yl]piperazine-1-sulfonyl methyl}-3-methylbutyryl)-oxazolidin-2-one (0.312 g), to give the title compound as a white solid (0.077 g, 33%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-53332be4c8d34fb49dfa54f8f777c2c0
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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