Furan-2-boronic acid → 4-[4-(4-Furan-2-ylphenyl)piperazine-1-sulfonylmethyl]-tetrahydropyran-4carboxylic acid-N-hydroxyamide

HRID 393747Notes

Reaction equation

HRID 393747 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C1C=CC(N2CCN(S(CC(C(C)C)C(O)=O)(=O)=O)CC2)=CC=1.[OH:29][NH:30][C:31]([C:33]1([CH2:39][S:40]([N:43]2[CH2:48][CH2:47][N:46]([C:49]3[CH:54]=[CH:53][C:52](Br)=[CH:51][CH:50]=3)[CH2:45][CH2:44]2)(=[O:42])=[O:41])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:32].O1C=CC=C1B(O)O>>[OH:29][NH:30][C:31]([C:33]1([CH2:39][S:40]([N:43]2[CH2:48][CH2:47][N:46]([C:49]3[CH:54]=[CH:53][C:52]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[CH:51][CH:50]=3)[CH2:45][CH2:44]2)(=[O:42])=[O:41])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:32]

Participants

4

Reactant 3

HCID 2734357Furan-2-boronic acidHCID 226467422-[4-(4-Furan-2-yl-phenyl)piperazine-1-sulfonylmethyl]-3-methylbutyric acidHCID 865847694-[4-(4-Bromophenyl)piperazine-1-sulfonylmethyl]-tetrahydropyran-4-carboxylic acid hydroxyamide

Product 1

HCID 865847704-[4-(4-Furan-2-ylphenyl)piperazine-1-sulfonylmethyl]-tetrahydropyran-4carboxylic acid-N-hydroxyamideYield 14%

Procedure

Prepared according to the method for the preparation 2-[4-(4-Furan-2-yl-phenyl)piperazine-1-sulfonylmethyl]-3-methylbutyric acid, from 4-[4-(4-bromophenyl)piperazine-1-sulfonylmethyl]tetrahydropyran-4-carboxylic acid hydroxyamide (0.249 g) and furan-2-boronic acid (0.066 g), to give the title compound as a cream solid (0.034 g, 14%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-01e3b69b729f4a39aeeb0d210da724b6
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

Loading…