p-Toluenesulfonic acid monohydrate → 1-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-4-hydroxyimino-7-methyl-6,7-dihydropyrrolo[2,3-c]azepin-8(1H,5H)-one p-toluenesulfonate

HRID 275002Notes

Reaction equation

HRID 275002 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[C:23](=[O:31])[N:24]([CH3:30])[CH2:25][CH2:26][C:27](=[N:28][OH:29])[C:21]=4[CH:20]=[CH:19]3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.O.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([OH:44])(=[O:43])=[O:42])=[CH:37][CH:36]=1>C(O)C>[C:35]1([CH3:45])[CH:36]=[CH:37][C:38]([S:41]([OH:44])(=[O:42])=[O:43])=[CH:39][CH:40]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[C:23](=[O:31])[N:24]([CH3:30])[CH2:25][CH2:26][C:27](=[N:28][OH:29])[C:21]=4[CH:20]=[CH:19]3)[CH2:10][CH2:9]2)=[O:7])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 850656071-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-4-hydroxyimino-7-methyl-6,7-dihydropyrrolo[2,3-c]azepine-8-(1H,5H)-one

Product 1

HCID 884037131-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-4-hydroxyimino-7-methyl-6,7-dihydropyrrolo[2,3-c]azepin-8(1H,5H)-one p-toluenesulfonateYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.0 g (11.0 mmol) of Compound 61 obtained in Example 24 and 2.1 g (11.0 mmol) of p-toluenesulfonic acid monohydrate was heated in 120 ml of ethanol, so that the latter compounds were dissolved. The resultant mixture was allowed to cool down, whereby 6.5 g of the title compound were obtained as colorless crystals (yield: 92%).

Workup

  1. dissolutionwere dissolved
  2. temperatureto cool down

Sources & evidence

ORD record
ord-2bbc72a12fb94a2e86f511dfd2a986f2
Source dataset
uspto-grants-1995_02
Patent number
US05391731

Reaction notes

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