HCID 69810160, compound → 4-Toluenesulfonyl chloride

HRID 2381181Notes

Reaction equation

HRID 2381181 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C@H:7]([C:21]([OH:23])=[O:22])[CH2:6]1)=[O:4].[ClH:24].[CH3:25][O:26][C:27]([C@H:29]1[CH2:34][CH2:33][NH:32][C@H:31]([C:35]([OH:37])=[O:36])[CH2:30]1)=[O:28]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[C@@H:7]([C:21]([OH:23])=[O:22])[CH2:6]1)=[O:4].[ClH:24].[CH3:25][O:26][C:27]([C@@H:29]1[CH2:34][CH2:33][NH:32][C@@H:31]([C:35]([OH:37])=[O:36])[CH2:30]1)=[O:28].[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([Cl:24])(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 69810160HCID 69810160, compoundHCID 69811508HCID 69811508, compound

Product 3

HCID 73974-Toluenesulfonyl chlorideHCID 69810517HCID 69810517, compoundHCID 69813058HCID 69813058, compound

Procedure

In analogy to example 36 step A) the desired racemic mixture of (2S,4S)-1-(toluene-4-sulfonyl)-piperidine-2,4-dicarboxylic acid 4-methyl ester and (2R,4R)-1-(toluene-4-sulfonyl)-piperidine-2,4-dicarboxylic acid 4-methyl ester (0.35 g) was obtained from the reaction of a racemic mixture of (2S,4S)-piperidine-2,4-dicarboxylic acid 4-methyl ester hydrochloride and (2R,4R)-piperidine-2,4-dicarboxylic acid 4-methyl ester hydrochloride (0.3 g) with 4-methyl-benzenesulfonyl chloride (0.294 g) as a white solid. MS (ESI): 342.06 (MH+).

Sources & evidence

ORD record
ord-857aaf1b68fe4affbc4725b4a819802b
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

Loading…