HCID 53681655, compound → HCID 23468129, compound

HRID 28215Notes

Reaction equation

HRID 28215 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][S:12][CH:11]2[CH2:16][CH:17]=[CH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=[O:23])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][S:12][CH:11]2[CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=[O:23])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 53681655HCID 53681655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23468129HCID 23468129, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propenyl}benzoic acid (7.8 g., 0.02 mole) in ethanol (125 ml.) is hydrogenated over 2.5 g. of a 5% Pd on charcoal catalyst at 1 atmosphere pressure and 27° C. When the theoretical amount (0.02 mole) of hydrogen has been absorbed, the catalyst is filtered off, the solvent evaporated, and the residue chromatographed on silica gel with 4% methanol in chloroform as the eluant. The title compound is obtained as a colorless, viscous oil.

Workup

  1. customat 1 atmosphere pressure and 27° C
  2. filtrationthe catalyst is filtered off
  3. customthe solvent evaporated
  4. customthe residue chromatographed on silica gel with 4% methanol in chloroform as the eluant

Sources & evidence

ORD record
ord-accbc80711cd4fed92cf4c23a8ce2cf4
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

Loading…