Lithium Hydroxide → (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid

Reaktionsgleichung

C[O:2][C:3](=[O:15])[C@@H:4]([OH:14])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Li+]>>[CH2:7]([S:6][CH2:5][C@H:4]([OH:14])[C:3]([OH:15])=[O:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

Edukt 2

HCID 3939Lithium Hydroxide

HCID 59639322(R)-3-Benzylsulfanyl-2-hydroxy-propionic acid methyl ester

Produkt 1

HCID 10059030(R)-3-Benzylsulfanyl-2-hydroxy-propionic acidAusbeute 46 %

Versuchsvorschrift

This reaction was performed as previously described by Deechongkit, S.; You, S.-L.; Kelly, J. W. Org. Lett. 2004, 6, 497, using (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid methyl ester 110b and lithium hydroxide. (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid 110c (3.08 g, 14.51 mmol, 46%) was isolated as a viscous oil: MS calcd. for C10H12O3S (M+Na+) 235.1. found 235.3.

Quellen und Nachweise

ORD-Eintrag: ord-bcb8eaa4c4504401886fac377227fe7a
Quelldatensatz: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07314872B2

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