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

HRID 1005880Notes

Reaction equation

HRID 1005880 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:73])[C@H:45]([CH2:49][S:50]([N:53]1[CH2:58][CH2:57][N:56]([C:59]2[N:64]=[CH:63][C:62]([C:65]3[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[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:72][C:67]1[CH:66]=[C:65]([C:62]2[CH:63]=[N:64][C:59]([N:56]3[CH2:57][CH2:58][N:53]([S:50]([CH2:49][C@H:45]([CH:46]([CH3:48])[CH3:47])[C:44]([OH:73])=[O:21])(=[O:52])=[O:51])[CH2:54][CH2:55]3)=[N:60][CH:61]=2)[CH:70]=[CH:69][C:68]=1[Cl:71]

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197494-(R)-Benzyl-3-(2-(R)-{4-[5-(3,4-dichlorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyryl)-oxazolidin-2-one

Product 1

HCID 235197352-(R)-{4-[5-(3,4-Dichlorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidYield 73%

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-(3,4-dichlorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one (0.51 g), to give the title compound as a pale yellow solid (0.27 g, 73%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-20b3bac40c194e7d8d1e140afd00cb90
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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