1-Chloro-4-acetoxynonane → 7-[N-(4(R)-hydroxy-2-nonynyl)acetamido]heptanoic acid
Reaction equation
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]Participants
4
Procedure
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).
Sources & evidence
- ORD record
- ord-5b5c471a16bb4f09be752429d36d7812
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03987091
Reaction notes
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