N-Methyl-1-(2-methylimidazo[1,2-a]pyridin-6-yl)-2-oxocyclohexanecarbothioamide → (+)-N-methyl-1-(2-methylimidazo[1,2-a]-pyridin-6-yl)-2-oxocyclohexanecarbothioamide (+)-dibenzoyl-D-tartrate

HRID 1757117Notes

Reaction equation

HRID 1757117 reaction equation
O.[C:2]([C@:10]([C:25]([OH:27])=[O:26])([OH:24])[C@:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:15])[C:12]([OH:14])=[O:13])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:28][NH:29][C:30]([C:32]1([C:39]2[CH:40]=[CH:41][C:42]3[N:43]([CH:45]=[C:46]([CH3:48])[N:47]=3)[CH:44]=2)[CH2:37][CH2:36][CH2:35][CH2:34][C:33]1=[O:38])=[S:31]>CC(C)=O.O>[C:16]([C@:11]([C:12]([OH:14])=[O:13])([OH:15])[C@:10]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:24])[C:25]([OH:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:28][NH:29][C:30]([C:32]1([C:39]2[CH:40]=[CH:41][C:42]3[N:43]([CH:45]=[C:46]([CH3:48])[N:47]=3)[CH:44]=2)[CH2:37][CH2:36][CH2:35][CH2:34][C:33]1=[O:38])=[S:31]

Participants

4

Reactant 2

HCID 19972896N-Methyl-1-(2-methylimidazo[1,2-a]pyridin-6-yl)-2-oxocyclohexanecarbothioamideHCID 122598382Dibezoyl-D-tartaric acid monohydrate

Product 1

HCID 131719090(+)-N-methyl-1-(2-methylimidazo[1,2-a]-pyridin-6-yl)-2-oxocyclohexanecarbothioamide (+)-dibenzoyl-D-tartrate

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent2×

Procedure

A solution of 20.26 g (53.8 mmol) of (+)-dibenzoyl-D-tartaric acid monohydrate in 110 ml of an acetone/water (4:1) mixture was added to a solution of 16.21 g (53.8 mmol) of the (±)-N-methyl-1-(2-methylimidazo[1,2-a]pyridin-6-yl)-2-oxocyclohexanecarbothioamide prepared in the Example 5 in 900 ml of an acetone/water (4:1) mixture. The obtained mixture was allowed to stand at room temperature for 2 hours, giving (+)-N-methyl-1-(2-methylimidazo[1,2-a]-pyridin-6-yl)-2-oxocyclohexanecarbothioamide (+)-dibenzoyl-D-tartrate as a colorless prism crystal. This crystal (14.6 g, 95% ee or above) was filtered out.

Sources & evidence

ORD record
ord-f71d03ae14d148f9a9735ee0c3932742
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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