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

HRID 1729927Notes

Reaction equation

HRID 1729927 reaction equation
ClCCCC([O:11]C(=O)C)CCCCC.ClCCCC(OC(=O)C)(C)CCCCC.C([O:33][C:34](C)([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:35][CH2:36][CH2:37][N:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49]CC)=[O:48])[C:39]#[N:40])(=O)C>>[OH:33][C@H:34]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:35]#[C:36][CH2:37][N:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[C:39]#[N:40].[OH:33][C@H:34]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:35]#[C:36][CH2:37][N:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[C:39]([NH2:40])=[O:11]

Participants

5

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 203860911-Chloro-4-acetoxy-4-methylnonaneHCID 86734154ethyl 7-[N-(4-acetoxy-4-methylnonyl)-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-chloro-4-acetoxy-4-methylnonane (Example R). The product of Step A is thus ethyl 7-[N-(4-acetoxy-4-methylnonyl)-cyanamido]heptanoate. The subsequent steps yield 7-[N-(4-hydroxy-4-methylnonyl)cyanamido]heptanoic acid (B) and 7-[1-(4-hydroxy-4-methylnonyl)ureido]heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-e1e615f9c6f34bf98bbf2786b760cf0c
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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