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

HRID 1729924Notes

Reaction equation

HRID 1729924 reaction equation
ClCCCC([O:11]C(=O)C)CCCCC.ClCCCC(OC(=O)C)CCCCC(F)(F)F.C([O:35][CH:36]([CH2:54][CH2:55][CH2:56][CH2:57][C:58](F)(F)F)[CH2:37][CH2:38][CH2:39][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51]CC)=[O:50])[C:41]#[N:42])(=O)C>>[OH:35][C@H:36]([CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:37]#[C:38][CH2:39][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[C:41]#[N:42].[OH:35][C@H:36]([CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:37]#[C:38][CH2:39][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[C:41]([NH2:42])=[O:11]

Participants

5

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 203860351-Chloro-4-acetoxy-9,9,9-trifluorononaneHCID 86734151ethyl 7-[N-(4-acetoxy-9,9,9-trifluorononyl)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-9,9,9trifluorononane (Example E). The product of Step A is thus ethyl 7-[N-(4-acetoxy-9,9,9-trifluorononyl)cyanamido]heptanoate. The subsequent steps yield 7-[N-(4-hydroxy-9,9,9-trifluorononyl)cyanamido]heptanoic acid (B) and 7-[1-(4-hydroxy-9,9,9-trifluorononyl)-ureido]heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-53fb2d7481df4b229b297e566f1a6ecb
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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