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

HRID 393745Notes

Reaction equation

HRID 393745 reaction equation
FC1C=CC(C2C=NC(N3CCN(S(C[C@H](C(C)C)C(O)=O)(=O)=[O:21])CC3)=NC=2)=CC=1.C([C@@H]1COC(=O)N1[C:44](=[O:72])[C@H:45]([CH2:49][S:50]([N:53]1[CH2:58][CH2:57][CH:56]([C:59]2[N: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:67]=[CH:66][C:65]([C:62]2[CH:61]=[N:60][C:59]([CH:56]3[CH2:57][CH2:58][N:53]([S:50]([CH2:49][C@H:45]([CH:46]([CH3:48])[CH3:47])[C:44]([OH:21])=[O:72])(=[O:51])=[O:52])[CH2:54][CH2:55]3)=[N:64][CH:63]=2)=[CH:70][CH:69]=1

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197514-(R)-Benzyl-3-(2-(R)-{4-[5-(4-chlorophenyl)pyrimidin-2-yl]piperidine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one

Product 1

HCID 235197372-(R)-{4-[5-(4-Chlorophenyl)pyrimidin-2-yl]piperidine-1-sulfonylmethyl}-3-methylbutyric acidYield 90%

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)pyrimidin-2-yl]piperidine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one (0.275 g), to give the title compound as a white solid (0.184 g, 90%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-325b98d401704678a3ae7df9f1bb97ea
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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