1-Chloro-4-acetoxynonane → 7-[N-(4(R)-hydroxy-2-nonynyl)acetamido]heptanoic acid

Reaktionsgleichung

ClCCCC(OC(=O)C)CCCCC.BrCC#C[C@H](OC(=O)C)CCCCC.C([O:32][C@H:33]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:34]#[C:35][CH2:36][N:37]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49]CC)=[O:48])[C:38](=[O:40])[CH3:39])(=O)C>>[OH:32][C@H:33]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:34]#[C:35][CH2:36][N:37]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[C:38](=[O:40])[CH3:39]

Komponenten

Edukt 3

HCID 131047161-Chloro-4-acetoxynonane

HCID 227938161-bromo-4(R)-acetoxy-2-nonyne

HCID 22793824ethyl 7-[N-(4(R)-acetoxy-2-nonynyl)-acetamido]heptanoate

Produkt 1

HCID 227938207-[N-(4(R)-hydroxy-2-nonynyl)acetamido]heptanoic acid

Versuchsvorschrift

The snthesis of this compound is carried out as described in Example 2 except that, in Step B, the 1-chloro-4-acetoxynonane is replaced by an equimolar amount of 1-bromo-4(R)-acetoxy-2-nonyne (Example J). The product of Step B is ethyl 7-[N-(4(R)-acetoxy-2-nonynyl)-acetamido]heptanoate. The subsequent step yields 7-[N-(4(R)-hydroxy-2-nonynyl)acetamido]heptanoic acid (C). The product of Step C is hydrogenated over a platinum on charcoal catalyst to afford 7-[N-(4(R)-hydroxynonyl)-acetamido]heptanoic acid (D).