Hydrochloric Acid → 2-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetic acid

HRID 1695906Notes

Reaction equation

HRID 1695906 reaction equation
[CH2:1]([N:6]1[C:10](=[O:11])[C:9](=[CH:12][C:13]([O:15]CC)=[O:14])[S:8][CH:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([N:6]1[C:10](=[O:11])[C:9](=[CH:12][C:13]([OH:15])=[O:14])[S:8][CH:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 72325412Ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetate

Product 1

HCID 723254372-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetic acidYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetate (0.031 g, 0.1 mmol) and aq. NaOH (0.3 ml of 1 N) in MeOH was stirred at 40° C. for 2 hours. HCl (0.5 ml of 1 N) was added and the MeOH was evaporated. Water and EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc (2×), all organic layers were combined, dried (MgSO4) and evaporated to dryness to give the desired product as an orange oil (11 mg, 36%).

Workup

  1. customthe MeOH was evaporated
  2. additionWater and EtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f79a315b39934501886143c1f76a8e7e
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

Loading…