Ethyl 7-(methanesulfinamido)heptanoate → ethyl 7-[N-(4-acetoxy-(E)-2-nonenyl)methanesulfonamido]heptanoic acid

HRID 372532Notes

Reaction equation

HRID 372532 reaction equation
[C:1](ONS(C)(=O)=O)(=O)[CH2:2]CCCCC.CS(NCCCCCCC(OCC)=O)=[O:17].[C:30]([O:33][CH:34]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:35][CH2:36][CH2:37][N:38]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]CC)=[O:49])[S:39]([CH3:41])=[O:40])(=[O:32])[CH3:31]>>[CH2:1]([CH:47]([CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][N:38]([CH2:37]/[CH:36]=[CH:35]/[CH:34]([O:33][C:30](=[O:32])[CH3:31])[CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[S:39]([CH3:41])(=[O:40])=[O:17])[C:48]([OH:50])=[O:49])[CH3:2]

Participants

4

Reactant 3

HCID 20327657Ethyl 7-(methanesulfinamido)heptanoateHCID 20327711ethyl 7-[N-(4-acetoxynonyl)methanesulfinamido]heptanoateHCID 86735728Methanesulfonamido heptanoate

Product 1

HCID 20327696ethyl 7-[N-(4-acetoxy-(E)-2-nonenyl)methanesulfonamido]heptanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 1 except that, in Step A, the ethyl 7-(methanesulfonamido heptanoate is replaced by an equimolar amount of ethyl 7-(methanesulfinamido)heptanoate (Example T). The product of Step A is thus ethyl 7-[N-(4-acetoxynonyl)methanesulfinamido]heptanoate. The subsequent step yields 7-[N-(4-hydroxynonyl)methanesulfinamido]heptanoic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-89047b3fdc17496cb5c225c1e7bdfab1
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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