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

HRID 372526Notes

Reaction equation

HRID 372526 reaction equation
ClCCCC(OC(=O)C)CCCCC.ClCCCC(OC(=O)C)CCCC(C)(C)C.C([O:34][CH:35]([CH2:55][CH2:56][CH2:57][C:58](C)(C)[CH3:59])[CH2:36][CH2:37][CH2:38][N:39]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][C:50]([O:52]CC)=[O:51])[S:40]([CH3:43])(=[O:42])=[O:41])(=O)C>>[OH:34][C@H:35]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:36]#[C:37][CH2:38][N:39]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][C:50]([OH:52])=[O:51])[S:40]([CH3:43])(=[O:41])=[O:42]

Participants

4

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 20327702ethyl 7-[N-(4-acetoxy-8,8-dimethylnonyl)methanesulfonamido]heptanoateHCID 203860361-Chloro-4-acetoxy-8,8-dimethylnonane

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-8,8-dimethylnonane (Example D). The product of Step A is thus ethyl 7-[N-(4-acetoxy-8,8-dimethylnonyl)methanesulfonamido]heptanoate. The subsequent step yields 7-[N-(4-hydroxy-8,8-dimethylnonyl)methanesulfonamido]heptanoic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-3537bba2a92a48eaba1ffc3dd9365116
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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