Hydrochloric Acid → 4-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid

HRID 28209

Reaction equation

HRID 28209 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[C:13](=[O:14])[CH2:12][S:11][CH:10]2[CH2:15][CH2:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-:27].[Na+].Cl>FC(F)(F)C(O)=O.O>[OH:27][C:1]1([CH2:7][CH2:8][N:9]2[C:13](=[O:14])[CH2:12][S:11][CH:10]2[CH2:15][CH2:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 233395764-{3-[3-[2-(1-Cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

Product 1

HCID 1750274-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-{3-[3-[2-(1-Cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (3.7 g., 0.01 mole) in trifluoroacetic acid (20 ml.) is allowed to stand at 25° C. for 4 hours. Excess trifluoroacetic acid is then removed by evaporation at reduced pressure. The oily residue is dissolved in a solution of sodium hydroxide (2.0 g., 0.05 mole) in water (40 ml.). The basic solution is acidified with 2 N hydrochloric acid. The title compound precipitates as a solid. Recrystallization from acetonitrile-water yields the purified title compound, m.p. 147°-148° C.

Workup

  1. customExcess trifluoroacetic acid is then removed by evaporation at reduced pressure
  2. customThe title compound precipitates as a solid
  3. customRecrystallization from acetonitrile-water
  4. customyields the
  5. custompurified title compound, m.p. 147°-148° C.

Sources & evidence

ORD record
ord-5afbe54c82b54ebfab0751091d87a832
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Linked notes

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