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

HRID 1005864Notes

Reaction equation

HRID 1005864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([CH2:23][C@H:24]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])[CH2:16][CH2:15]3)=N[CH:13]=2)=[CH:4][CH:3]=1.[CH2:31]([C@@H]1COC(=O)N1C(=O)[C@H](CS(N1CCN(C2C=CC(C3C=CC(F)=CC=3)=CN=2)CC1)(=O)=O)C(C)C)C1C=CC=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:31][C:11]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([CH2:23][C@H:24]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:27])=[O:26])(=[O:21])=[O:22])[CH2:16][CH2:15]3)=[N:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197534-(R)-Benzyl-3-(2-(R)-{4-[5-(4-fluorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyryl)-oxazolidin-2-one

Product 1

HCID 235197422-(R)-{4-[5-(4-Fluorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidYield 59%

Procedure

Prepared according to the method for the preparation of 2-(R)-{4-[5-(4-fluoro-phenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid, from 4-(R)-benzyl-3-(2-(R)-{4-[5-(4-fluorophenyl)pyridin-2-yl]piperazine-1-sulfonyl methyl}-3-methylbutyryl)-oxazolidin-2-one (0.167 g), to yield the title compound as a white solid (0.072 g, 59%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-feb688ccc7c24e31bfc0eb4460bb7dd8
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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