Diethyl Ether → 1-[([4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid

HRID 1627486Notes

Reaction equation

HRID 1627486 reaction equation
[OH-].[Na+].C1(C[O:10][C:11]([C:13]2([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[N:29]=[C:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)[S:31][CH:32]=4)=[CH:24][CH:23]=3)=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])C=CC=CC=1.CCOCC>O1CCCC1>[CH3:39][N:36]1[CH2:35][CH2:34][N:33]([C:30]2[S:31][CH:32]=[C:28]([C:25]3[CH:24]=[CH:23][C:22]([C:20]([NH:19][C:13]4([C:11]([OH:12])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:21])=[CH:27][CH:26]=3)[N:29]=2)[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 576728201-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

Product 1

HCID 576728871-[([4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35 ml of 2N aqueous sodium hydroxide solution was added to a solution of 11.8 g (23.0 mmol) of 1-[[[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester in 120 ml of tetrahydrofuran, and the mixture was heated under reflux for 15 hours. Ether was added to the reaction solution and the aqueous layer was separated. Concentrated hydrochloric acid was added to the separated aqueous layer to neutralize it, and the precipitated crystal was collected by filtration to obtain 6.60 g (67%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. customthe aqueous layer was separated
  4. additionConcentrated hydrochloric acid was added to the separated aqueous layer
  5. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-45743d1fa97f41239d749110995fa0a7
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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