Pyridinium chloride → HCID 68292072, compound

HRID 529449Notes

Reaction equation

HRID 529449 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=2)[C:15]([OH:17])=[O:16])[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>O>[OH:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C@@H:14]([CH2:13][CH2:12][C@H:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=2)[C:9]([OH:11])=[O:10])[C:15]([OH:17])=[O:16])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 68291970HCID 68291970, compound

Product 1

HCID 68292072HCID 68292072, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To a round bottom flask was added (2R,5R)-2,5-bis(4-methoxybenzyl)hexanedioic acid (124 mg, 0.321 mmol) and pyridine hydrochloride (371 mg, 3.21 mmol). The reaction was stirred at 160° C. for 20 min. After cooling to rt, the reaction was diluted with water and extracted with EtOAc (2×15 mL). The combined EtOAc extracts were concentrated in vacuum. The resulting residue was purified using RP prep-HPLC (Method B) to give (2R,5R)-2-(4-hydroxybenzyl)-5-(4-methoxybenzyl)hexanedioic acid (37 mg, 0.099 mmol, 31% yield) as white solid.

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×15 mL)
  3. concentrationThe combined EtOAc extracts were concentrated in vacuum
  4. customThe resulting residue was purified

Sources & evidence

ORD record
ord-04d9f482d6444fdab8da304f36b3d2b2
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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