HCID 23513780, compound → HCID 23513915, compound

HRID 278326Notes

Reaction equation

HRID 278326 reaction equation
C(OC1C=CC(S(C2(C(O)=O)CCCN(CC3C=CC(Cl)=CC=3)C2)(=O)=O)=CC=1)C#CC.Cl.[CH2:33]([O:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([C:47]2([C:61]([NH:63][OH:64])=[O:62])[CH2:52][CH2:51][CH2:50][N:49]([CH2:53][C:54]3[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=3)[CH2:48]2)(=[O:46])=[O:45])=[CH:40][CH:39]=1)[C:34]#[C:35][CH3:36]>>[CH2:33]([O:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([C:47]2([C:61]([NH:63][OH:64])=[O:62])[CH2:52][CH2:51][CH2:50][N:49]([CH2:53][C:54]3[CH:55]=[CH:56][C:57]([Cl:60])=[CH:58][CH:59]=3)[CH2:48]2)(=[O:45])=[O:46])=[CH:40][CH:39]=1)[C:34]#[C:35][CH3:36]

Participants

3

Reactant 2

HCID 23513780HCID 23513780, compoundHCID 86757881HCID 86757881, compound

Product 1

HCID 23513915HCID 23513915, compoundYield 43%

Procedure

Starting from 3-{[4-(2-butynyloxy)phenyl]sulfonyl}-1-(4-chlorobenzyl)-3-piperidinecarboxylic acid (1.1 g, 2.4 mmol) and and following the procedure as outlined in example 1, (step 8), 0.48 g of 3-{[4-(2-butynyloxy)phenyl]sulfonyl}-1-(4-chlorobenzyl)-3-N-hydroxy-3-piperidinecarboxamide hydrogen chloride was isolated as a white solid. Yield 43%; mp 124.4° C.; MS (ES): m/z: 477.1 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ2.0 (m, 2H), 3.39 (m, 5H), 4.27 (d, 2H), 4.89 (m, 2H), 7.14 (d, 2H), 7.15 (m, 4H), 7,61 (d, 2H), 8.95 (s, 1H), 9.46 (s, 1H).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-f941b5518b1b4cb39eb82809baba76b3
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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