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

HRID 1729923Notes

Reaction equation

HRID 1729923 reaction equation
ClCCCC([O:11]C(=O)C)CCCCC.ClCCCC(OC(=O)C)CCCC(C)(C)C.C([O:34][CH:35]([CH2:53][CH2:54][CH2:55][C:56]([CH3:59])(C)[CH3:57])[CH2:36][CH2:37][CH2:38][N:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]CC)=[O:49])[C:40]#[N:41])(=O)C>>[OH:34][C@H:35]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:36]#[C:37][CH2:38][N:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[C:40]#[N:41].[OH:34][C@H:35]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:59])[C:36]#[C:37][CH2:38][N:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[C:40]([NH2:41])=[O:11]

Participants

5

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 203860361-Chloro-4-acetoxy-8,8-dimethylnonaneHCID 86734150ethyl 7-[N-(4-acetoxy-8,8-dimethylnonyl)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-8,8-dimethylnonane (Example D). The product of Step A is thus ethyl 7-[N-(4-acetoxy-8,8-dimethylnonyl)cyanamido]heptanoate. The subsequent steps yield 7-[N-(4-hydroxy-8,8-dimethylnonyl)cyanamido]-heptanoic acid (B) and 7-[1-(4-hydroxy-8,8-dimethylnonyl)ureido]heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-1a4fb72bb29647129ed58f057a595747
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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