Hydrochloric Acid → HCID 58136371, compound

HRID 877160Notes

Reaction equation

HRID 877160 reaction equation
[CH:1]1([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:22]([CH3:23])=[C:21]([CH2:24][CH:25]([CH3:27])[CH3:26])[S:20][C:19]3=[O:28])=[CH:13][CH:12]=2)[C:7]([O:9]C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Na+].Cl>C1COCC1>[CH:1]1([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:22]([CH3:23])=[C:21]([CH2:24][CH:25]([CH3:26])[CH3:27])[S:20][C:19]3=[O:28])=[CH:13][CH:12]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 58136671HCID 58136671, compound

Product 1

HCID 58136371HCID 58136371, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.01 g (2.515 mmol) of methyl cyclopentyl(4-{[4-methyl-5-(2-methylpropyl)-2-oxo-1,3-thiazol-3(2H)-yl]methyl}phenyl)acetate were dissolved in 30 ml of THF, and 10 ml of methanol and 10 ml of 1 N aqueous sodium hydroxide solution were added. The reaction solution was stirred at room temperature for 2 days. A further 5 ml of 1 N aqueous sodium hydroxide solution were then added, and the mixture was stirred at RT for another 2 days. 20 ml of 1 N hydrochloric acid were then added, and the reaction mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed on a rotary evaporator. This gave 956 mg (2.47 mmol, 98% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at RT for another 2 days
  2. extractionthe reaction mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-29ad2bcdb9a24fcf9961ae0db6cb045b
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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