Hydrogen Bromide → HCID 68311219, compound

HRID 529448Notes

Reaction equation

HRID 529448 reaction equation
C[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.Br>C(O)(=O)C>[OH: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:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[C:15]([OH:17])=[O:16])[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68291970HCID 68291970, compound

Product 1

HCID 68311219HCID 68311219, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a round bottom flask was added (2R,5R)-2,5-bis(4-methoxybenzyl)hexanedioic acid (10 mg, 0.026 mmol) and 30% HBr in acetic acid (0.5 mL). The reaction was stirred at 120° C. for 2 days. The solvent was removed and the residue was purified by RP prep-HPLC. The fraction was concentrated to give (2R,5R)-2,5-bis(4-hydroxybenzyl)hexanedioic acid (3.0 mg, 8.4 μmol, 32% yield) as an off-white solid. Anal. Calcd. for C20H22O6 m/z 358.3. found: 357.3 (M−H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by RP prep-HPLC
  3. concentrationThe fraction was concentrated

Sources & evidence

ORD record
ord-c6a29ab8eb9b4e36bfb4b02192236dbe
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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