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

HRID 1729913Notes

Reaction equation

HRID 1729913 reaction equation
ClCCCC([O:11]C(=O)C)CCCCC.BrCC#CC(OC(=O)C)CCCCC.C([O:32][CH: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][CH: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

4

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 203861201-Bromo-4-acetoxy-2-nonyneHCID 86734140ethyl 7-[N-(4-acetoxy-2-nonynyl)cyanamido]heptanoate

Product 1

HCID 215014367-[1-(4-Hydroxy-2-nonynyl)ureido]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-acetoxy-2-nonyne (Example I, Step 3). The product of Step A is thus ethyl 7-[N-(4-acetoxy-2-nonynyl)cyanamido]heptanoate. The subsequent steps yield 7-[N-(4-hydroxy-2-nonynyl)cynamido]heptanoic acid (B), and 7-[1-(4-hydroxy-2-nonynyl)ureido]heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-76b38dea4bcc47c4911df1a52b412615
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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