Ethanol → 4-[(6-Chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine-2-carboxylic Acid

HRID 352958

Reaction equation

HRID 352958 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][C:25]4[CH2:26][NH:27][CH:28]([CH3:32])[CH2:29][C:30]=4[N:31]=3)=[O:22])[CH:17]([C:33]([O:35]CC)=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(O)C.[OH-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][C:25]4[CH2:26][NH:27][CH:28]([CH3:32])[CH2:29][C:30]=4[N:31]=3)=[O:22])[CH:17]([C:33]([OH:35])=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 227100024-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-(ethoxycarbonyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine

Product 1

HCID 227103534-[(6-Chloronaphthalen-2-yl)sulfonyl]-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (10 ml), 4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-(ethoxycarbonyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine (2.08 g) was dissolved, followed by the addition of ethanol (20 ml) and a 1N aqueous solution (3.70 ml) of sodium hydroxide. The resulting mixture was stirred at room temperature for 1 hour. After concentration of the reaction mixture under reduced pressure, the residue was added with water (20 ml). The precipitate thus formed was collected by filtration, whereby the title compound (1.39 g) was obtained as a pale yellow foam.

Workup

  1. customThe precipitate thus formed
  2. filtrationwas collected by filtration, whereby the title compound (1.39 g)
  3. customwas obtained as a pale yellow foam

Sources & evidence

ORD record
ord-90f2c4195fba489180b31f4618eb5a99
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Linked notes

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