1-Chloro-4-acetoxynonane → 7-[1-(4(R)-hydroxy-2-nonynyl)ureido]heptanoic acid
反応式
ClCCCC([O:11]C(=O)C)CCCCC.BrCC#C[C@@H](OC(=O)C)CCCCC.C([O:32][C@@H:33]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:34]#[C:35][CH2:36][N:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48]CC)=[O:47])[C:38]#[N:39])(=O)C>>[OH:32][C@H:33]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:34]#[C:35][CH2:36][N:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([OH:48])=[O:47])[C:38]#[N:39].[OH:32][C@H:33]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:34]#[C:35][CH2:36][N:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([OH:48])=[O:47])[C:38]([NH2:39])=[O:11]参加物
5
実験手順
The synthesis of this compound is carried out as described in Example 1 except that, in Step a, the 1-chloro-4-acetoxynonane is replaced by an equimolar amount of 1-bromo-4(S)-acetoxy-2-nonyne (Example K). The product of Step A is thus ethyl 7-[N-(4(S)-acetoxy-2-nonynyl)cyanamido]heptanoate. The subsequent steps yield 7-[N-(4(S)-hydroxy-2-nonynyl)-cyanamido]heptanoic acid (B) and 7-[1-(4(S)-hydroxy-2-nonynyl)ureido]heptanoic acid (C). The product of Step C is hydrogenated over a platinum on charcoal catalyst to afford 7-[1-(4(S)-hydroxy-nonyl)ureido]heptanoic acid.