3-Hydroxypiperidine → Rac-2-(3-hydroxy-piperidin-1-yl)-5-methylsulfamoyl-benzoic acid

HRID 32746

Reaction equation

CS(C1C=CC(N2CCCC2)=C(C=1)C(O)=O)(=O)=O.Cl[C:20]1[CH:28]=[CH:27][C:26]([S:29](=[O:33])(=[O:32])[NH:30][CH3:31])=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].[OH:34][CH:35]1[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]1>>[OH:34][CH:35]1[CH2:40][CH2:39][CH2:38][N:37]([C:20]2[CH:28]=[CH:27][C:26]([S:29](=[O:33])(=[O:32])[NH:30][CH3:31])=[CH:25][C:21]=2[C:22]([OH:24])=[O:23])[CH2:36]1

Participants

Reactant 3

HCID 232933-Hydroxypiperidine

HCID 111724Benzoic acid, 2-chloro-5-[(methylamino)sulfonyl]-

HCID 597934895-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid

Product 1

HCID 59793580Rac-2-(3-hydroxy-piperidin-1-yl)-5-methylsulfamoyl-benzoic acidYield 15%

Procedure

The title compound was synthesised according to the procedure described for the synthesis of 5-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid (Example S) from 2-Chloro-5-methylsulfamoyl-benzoic acid and rac-3-hydroxy-piperidine and obtained in 15% yield. MS (m/e): 312.9 (MH− 100%).

Workup

customobtained in 15% yield

Sources & evidence

ORD record: ord-36919d26d00f4ef1a0e891b347c58139
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427612B2

Linked notes

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