Sodium Hydroxide → 4-{3-[3-[3-(1-Hydroxycyclohexyl)-(E)-2-propenyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

HRID 28220Notes

Reaction equation

HRID 28220 reaction equation
O1CCCCC1[O:7][C:8]1(/[CH:14]=[CH:15]/[CH2:16][N:17]2[C:21](=[O:22])[CH2:20][S:19][CH:18]2[CH2:23][CH2:24][CH2:25][C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32]CC)=[O:31])=[CH:28][CH:27]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH-].[Na+]>C(O)C.O>[OH:7][C:8]1(/[CH:14]=[CH:15]/[CH2:16][N:17]2[C:21](=[O:22])[CH2:20][S:19][CH:18]2[CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:35][CH:36]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86737243Ethyl 4-{3-[3-[3-(1-(Tetrahydro-2H-pyran-2-yloxy)cyclohexyl)-(E)-2-propenyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

Product 1

HCID 867372424-{3-[3-[3-(1-Hydroxycyclohexyl)-(E)-2-propenyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the ester product of Step B above (4.5 g., 8.7 mmole) and pyridinium tosylate (220 mg., 0.87 mmole) in ethanol (50 ml.) is let stand at 25° C. for 2.5 hours. To this reaction solution is added a solution of sodium hydroxide (1.2 g., 30 mmole) in water (12 ml.). The resulting soluton is let stand at 25° C. for 20 hours. The ethanol is then evaporated at reduced pressure. The residue is dissolved in water, and the solution acidified with 2 N hydrochloric acid to precipitate the product as a yellow gum. It is chromatographed on 60 g. of silica gel with elution by 2% methanol in chloroform. The purified title product is obtained as a yellowish, viscous oil weighing 2.4 g.; pmr (CDCl3) δ2.74 (2H, brt, CH2Ph), 3.55 (2H, brs, COCH2S), 4.70 (1H, brd, SCHN), 5.70 (2H, m, CH=CH), 6.53 (2H, brs, OH and CO2H).

Workup

  1. customThe ethanol is then evaporated at reduced pressure
  2. dissolutionThe residue is dissolved in water
  3. customto precipitate the product as a yellow gum
  4. customIt is chromatographed on 60 g
  5. washof silica gel with elution by 2% methanol in chloroform
  6. customThe purified title product
  7. customis obtained as a yellowish, viscous oil

Sources & evidence

ORD record
ord-b994fd18eb15482ab18345f20eba688c
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

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