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

HRID 258614Notes

Reaction equation

HRID 258614 reaction equation
ClCCCC(OC(=O)C)CCCCC.ClCCCC(OC(=O)C)CCCC=C.C([O:32][CH:33]([CH2:53][CH2:54][CH2:55][CH:56]=[CH2:57])[CH2:34][CH2:35][CH2:36][N:37]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]CC)=[O:49])[S:38]([CH3:41])(=[O:40])=[O:39])(=O)C>>[OH:32][C@H:33]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:34]#[C:35][CH2:36][N:37]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[S:38]([CH3:41])(=[O:39])=[O:40]

Participants

4

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 20327715ethyl 7-[N-(4-acetoxy-8-nonenyl)methanesulfonamido]heptanoateHCID 203860741-Chloro-4-acetoxy-8-nonene

Product 1

HCID 227984047-[N-(4(R)-hydroxy-2-nonynyl)methanesulfonamido]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-nonene. The product of Step A is thus ethyl 7-[N-(4-acetoxy-8-nonenyl)methanesulfonamido]heptanoate. The subsequent step yields 7-[N-(4-hydroxy-8-nonenyl)methanesulfonamido]heptanoic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-2508ae3c0bf2418e9574010ed1873717
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

Loading…