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

HRID 1729928Notes

Reaction equation

HRID 1729928 reaction equation
ClCCCC([O:11]C(=O)C)CCCCC.C(OC1(C#CCBr)CCCCCCC1)(=O)C.C([O:34][C:35]1([C:43]#[C:44][CH2:45][N:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([O:57]CC)=[O:56])[C:47]#[N:48])CC[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)(=O)C>>[OH:34][C@H:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:43]#[C:44][CH2:45][N:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([OH:57])=[O:56])[C:47]#[N:48].[OH:34][C@H:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:43]#[C:44][CH2:45][N:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([OH:57])=[O:56])[C:47]([NH2:48])=[O:11]

Participants

5

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 203222401-Acetoxy-1-(3-bromo-1-propynyl)cyclooctaneHCID 86734155ethyl 7-{N-[3-(1-acetoxycyclooctyl)-2-propyn-1-yl]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 a equimolar amount of -1-acetoxy-1-(3-bromo-1-propynyl)cyclooctane (Example Q). The product of Step A is thus ethyl 7-{N-[3-(1-acetoxycyclooctyl)-2-propyn-1-yl]cyanamido}heptanoate. The subsequent steps yield 7-{N-[3-(1-hydroxycyclooctyl)-2-propyn-1-yl]cyanamido}heptanoic acid (B) and 7-{1-[3-(1-hydroxycyclooctyl)-2-propyn-1-yl]ureido}heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-4c6a78eca3af4464ad741624d0fbb6bf
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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