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

HRID 393719Notes

Reaction equation

HRID 393719 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])[CH:45]([CH2:49][S:50]([N:53]1[CH2:58][CH2:57][CH:56]([O:59][C:60]2[CH:65]=[CH:64][C:63]([C:66]3[CH:71]=[CH:70][C:69]([F:72])=[CH:68][CH:67]=3)=[CH:62][N:61]=2)[CH2:55][CH2:54]1)(=[O:52])=[O:51])[CH:46]([CH3:48])[CH3:47])C1C=CC=CC=1>>[F:72][C:69]1[CH:68]=[CH:67][C:66]([C:63]2[CH:64]=[CH:65][C:60]([O:59][CH:56]3[CH2:57][CH2:58][N:53]([S:50]([CH2:49][C@H:45]([CH:46]([CH3:47])[CH3:48])[C:44]([OH:73])=[O:21])(=[O:51])=[O:52])[CH2:54][CH2:55]3)=[N:61][CH:62]=2)=[CH:71][CH:70]=1

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197484-(R)-benzyl-3-(2-{4-[5-(4-fluorophenyl)pyridin-2-yloxy]piperidine-1-sulfonyl methyl}-3-methyl-butyryl)oxazolidin-2-one

Product 1

HCID 235197402-(R)-{4-[5-(4-Fluorophenyl)pyridin-2-yloxy]piperidine-1-sulfonylmethyl}-3-methylbutyric acidYield 47%

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-{4-[5-(4-fluorophenyl)pyridin-2-yloxy]piperidine-1-sulfonyl methyl}-3-methyl-butyryl)oxazolidin-2-one (0.70 g) to yield the title compound as a cream solid (0.24 g, 47%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2729eadb63a043718e61be9cafc93f6b
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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