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

HRID 393723Notes

Reaction equation

HRID 393723 reaction equation
F[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:12][CH:13]=2)=[CH:4]C=1.C([C@@H]1COC(=O)[N:39]1C(=O)[C@H](CS(N1CCN(C2N=CC(C3C=NC=CC=3)=CN=2)CC1)(=O)=O)C(C)C)C1C=CC=CC=1>>[CH3:30][CH:28]([CH3:29])[C@@H:24]([CH2:23][S:20]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[N:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:39][CH:2]=[CH:7][CH:6]=3)=[CH:9][N:10]=2)[CH2:15][CH2:16]1)(=[O:22])=[O:21])[C:25]([OH:27])=[O:26]

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197564(R)-Benzyl-3-{3-methyl-2-(R)-[4-(5-pyridin-3-ylpyrimidin-2-yl)piperazine-1-sulfonylmethyl]butyryl}oxazolidin-2-one

Product 1

HCID 235197463-Methyl-2-(R)-[4-(5-pyridin-3-ylpyrimidin-2-yl)piperazine-1-sulfonylmethyl]butyric acidYield 61%

Procedure

Prepared according to the method for the preparation of 2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine1-sulfonylmethyl}-3-methylbutyric acid, from 4-(R)-benzyl-3-{3-methyl-2-(R)-[4-(5-pyridin-3-ylpyrimidin-2-yl)piperazine-1-sulfonylmethyl]butyryl}oxazolidin-2-one (0.353 g), to give the title compound as a white solid (0.157 g, 61%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-50918c4c7109439c936912ffc4265e4c
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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