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

HRID 1729925Notes

Reaction equation

HRID 1729925 reaction equation
ClCCCC([O:11]C(=O)C)CCCCC.C([O:18][CH:19]([CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH2:20][CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:24]#[N:25])(=O)C>>[OH:18][C@H:19]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:20]#[C:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:24]#[N:25].[OH:18][C@H:19]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:20]#[C:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:24]([NH2:25])=[O:11]

Participants

4

Reactant 2

HCID 131047161-Chloro-4-acetoxynonaneHCID 86734152ethyl 7-[N-(4-acetoxy-8-nonenyl)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-aceotoxy-8nonane. The product of Step A is thus ethyl 7-[N-(4-acetoxy-8-nonenyl)cyanamido]heptanoate. The subsequent steps yield 7-[N-(4-hydroxy-8-nonenyl)cyanamido]heptanoic acid (B) and 7-[1-(4-hydroxy-8-nonenyl)ureido]heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-e6201dce39224078a51999b5c19a1093
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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