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

HRID 1729914Notes

Reaction equation

HRID 1729914 reaction equation
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]

Participants

5

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 227938161-bromo-4(R)-acetoxy-2-nonyneHCID 86734142ethyl 7-[N-(4(R)-acetoxy-2-nonynyl)cyanamido]-heptanoate

Product 2

HCID 227942327-[1-(4(R)-hydroxy-2-nonynyl)ureido]heptanoic acidHCID 867341417-[N-(4-(R)-hydroxy-2-nonynyl)cyanamido]heptanoic acid

Procedure

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(R)-acetoxy-2-nonyne (Example J). The product of Step A is thus ethyl 7-[N-(4(R)-acetoxy-2-nonynyl)cyanamido]-heptanoate. The subsequent steps yield 7-[N-(4-(R)-hydroxy-2-nonynyl)cyanamido]heptanoic acid (B), and 7-[1-(4(R)-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(R)-hydroxynonyl)ureido]heptanoic acid.

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-1cc1233054814c399f50b6958e4da095
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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