Pyridinium chloride → HCID 68292015, compound

HRID 529447Notes

Reaction equation

HRID 529447 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][C@@H:6]([CH2:10][CH2:11][C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])[C:7]([OH:9])=[O:8].Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][C@@H:6]([CH2:10][CH2:11][C@H:12]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[C:13]([OH:15])=[O:14])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 68291958HCID 68291958, compound

Product 1

HCID 68292015HCID 68292015, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To a round bottom flask was added (2R,5R)-2-(3-Chlorobenzyl)-5-(4-methoxybenzyl)hexanedioic acid (24 mg, 0.061 mmol) and pyridine hydrochloride (71 mg, 0.61 mmol). The reaction was stirred at 160° C. for 10 min. After cooling to rt, the reaction was diluted with water and extracted with EtOAc (2×5 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-(3-chlorobenzyl)-5-(4-hydroxybenzyl)hexanedioic acid (14 mg, 0.037 mmol, 61% yield) as white solid. Anal. Calcd. for C20H21ClO5 m/z 376.3. found: 375.2 (M−H)+.

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×5 mL)
  3. concentrationThe combined EtOAc extracts were concentrated in vacuum
  4. customThe resulting residue was purified

Sources & evidence

ORD record
ord-36429c255d444d82a0d7d4adce33da21
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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