Hydrochloric Acid → 6,8-Bisbenzoylmercaptooctanoic benzoic anhydride

HRID 966134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966134
[C:1]([S:9][CH:10]([CH2:18][CH2:19][S:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]1[CH:33]([CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=O)SSC1.C1[C@@H](CCCCC(O)=O)SSC1.SC(CCS)CCCCC(O)=O.[BH4-].[Na+].C(Cl)(=O)C1C=CC=CC=1.Cl>O.C(N(CC)CC)C>[C:38]([O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([S:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:18][CH2:19][S:20][C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:40])[C:37]1[CH:29]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 421Dihydrolipoic AcidHCID 864alpha Lipoic acidHCID 6112Lipoic acidHCID 7412Benzoyl chlorideHCID 4311764Sodium borohydrideHCID 98448236,8-Bisbenzoylmercaptooctanoic acid

Produkt 1

HCID 865856116,8-Bisbenzoylmercaptooctanoic benzoic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

In overview, 6,8-Bisbenzoylmercaptooctanoic acid was prepared by a three step procedure from commercially available α-lipoic acid. The lipoic acid was first reduced to 6,8-bismercaptooctanoic acid with sodium borohydride in water under slightly alkaline conditions. The product was benzoylated with three equivalents of benzoyl chloride in the presence of triethylamine to scavenge the HCl byproduct to produce 6,8-bisbenzoylmercaptooctanoic benzoic anhydride. The anhydride was selectively hydrolyzed with dioxane/water to produce 6,8-bisbenzoylmercaptooctanoic acid without any undesired hydrolysis of the benzoylthio ester groups. The product was purified by column chromatography on Silica Gel. The purified acid was dissolved in methanol and converted to the sodium salt by the slow addition of an aqueous solution containing one mole equivalent of sodium bicarbonate.

Quellen und Nachweise

ORD-Eintrag
ord-7e197d3009fa4b5a87f2c5358fb40d02
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951887B2

Notizen zur Reaktion

Wird geladen…