反応 #1365698

ord-c6ada506e9ec4b2d84e95d340909fd15

反応方程式

[BH4-].[Na+]
Sodium borohydride
O=C(O)CCCC[C@@H]1CCSS1
lipoic acid
C1=CSSC1
dithiol
O=C(O)CCCC[C@@H]1CCSS1
lipoic acid
Cl
hydrochloric acid
O=C(O)CCCC[C@@H](S)CCS
dihydrolipoic acid
収率 80.0%

反応条件

温度
0°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The toluene layer was collected
  2. 2
    洗浄The aqueous layer was washed three times with 15 mL toluene
  3. 3
    乾燥dried with anhydrous magnesium sulfate
  4. 4
    ろ過filtered
  5. 5
    その他the solvent removed under vacuum

実験手順

The synthesis of a bidentate dithiol ligand was accomplished via the reduction of the coenzyme lipoic acid. The general procedure was described in I. C. Gunsalus, L. S. Barton, W. Gruber, J Am. Chem. Soc. 78:1763-1766 (1956). Sodium borohydride (1.2 g) was added in 30-50 mg portions to a stirring suspension of lipoic acid (6.0 g) in 117 mL of 0.25 M sodium bicarbonate in 0° C. water. The reaction was stirred for 45 minutes at 0° C., after which 100 mL toluene was added and the mixture was acidified to pH˜2 with hydrochloric acid. The toluene layer was collected and saved. The aqueous layer was washed three times with 15 mL toluene. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum, leaving behind the product dihydrolipoic acid as a yellow oil (yield 80%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06444143B1uspto-grants-2002_09