Ethyl 7-(methanesulfonamido)heptanoate → 7-[N-(4(R)-hydroxy-2-nonynyl)methanesulfonamido]heptanoic acid

HRID 258603Notes

Reaction equation

HRID 258603 reaction equation
CS(NCCCCCCC(OCC)=O)(=O)=O.C(S(NCCCCCCC(OCC)=O)(=O)=O)CC.C([O:38][CH:39]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:40][CH2:41][CH2:42][N:43]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][C:56]([O:58]CC)=[O:57])[S:44]([CH2:47]CC)(=[O:46])=[O:45])(=O)C>>[OH:38][C@H:39]([CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:40]#[C:41][CH2:42][N:43]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][C:56]([OH:58])=[O:57])[S:44]([CH3:47])(=[O:45])=[O:46]

Participants

4

Reactant 3

HCID 12150839Ethyl 7-(methanesulfonamido)heptanoateHCID 20327664Ethyl 7-(propanesulfonamido)heptanoateHCID 20327689ethyl 7-[N-(4-acetoxynonyl)propanesulfonamido]heptanoate

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 ethyl 7-(methanesulfonamido)heptanoate is replaced by an equimolar amount of ethyl 7-(propanesulfonamido)heptanoate (Example Q). The product of Step A is thus ethyl 7-[N-(4-acetoxynonyl)propanesulfonamido]heptanoate. The subsequent hydrolysis step yields 7-[N-(4-hydroxynonyl)-propanesulfonamido]heptanoic acid (B).

Workup

  1. customThe synthesis of this compound
  2. customThe subsequent hydrolysis step

Sources & evidence

ORD record
ord-6d264e4801ab48978eeed565d2095d2a
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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