Hydrogen Bromide → HCID 68292665, compound

HRID 529444Notes

Reaction equation

HRID 529444 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)[C:15]([OH:17])=[O:16])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br>C(O)(=O)C>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[C:15]([OH:17])=[O:16])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68292025HCID 68292025, compound

Product 1

HCID 68292665HCID 68292665, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a round bottom flask was added (2R,5R)-2-benzyl-5-(4-methoxybenzyl)hexanedioic acid (30 mg, 0.084 mmol) and 30% HBr in acetic acid (0.5 mL). The reaction was stirred at 120° C. for 16 h. Then the solvent was removed. The residue was purified by RP prep-HPLC (Method A). The fraction was concentrated to give (2R,5R)-2-benzyl-5-(4-hydroxybenzyl)hexanedioic acid (10 mg, 0.029 mmol, 35% yield) as an off-white solid.

Workup

  1. customThen the solvent was removed
  2. customThe residue was purified by RP prep-HPLC (Method A)
  3. concentrationThe fraction was concentrated

Sources & evidence

ORD record
ord-2c56fbe38ac94c3db713903b110b64ed
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…