Hydrochloric Acid → (R)-Dihydrolipoic acid

HRID 1278516

Reaktionsgleichung

Reaktionsgleichung von HRID 1278516
S1C=CCS1.[CH2:6]1[C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:9][S:8][CH2:7]1.[BH4-].[Na+].Cl>C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1.O>[CH2:12]([CH2:11][C@@H:10]([SH:9])[CH2:6][CH2:7][SH:8])[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6112Lipoic acid2×HCID 5253311,2-DithioleHCID 4311764Sodium borohydride

Produkt 1

HCID 9834298(R)-Dihydrolipoic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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%).

Aufarbeitung

  1. customThe toluene layer was collected
  2. washThe aqueous layer was washed three times with 15 mL toluene
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c6ada506e9ec4b2d84e95d340909fd15
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444143B1

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