Ethyl 7-bromoheptanoate → 7-{N-[4-hydroxy-5-(4-fluorophenoxy)-trans-2-pentenyl]methanesulfonamido}heptanoic acid

HRID 973193Notes

Reaction equation

HRID 973193 reaction equation
C(OC(COC1C=CC(F)=CC=1)/C=C/CNS(C)(=O)=O)(=O)C.C(OC(COC1C=CC(F)=CC=1)CCCNS(C)(=O)=O)(=O)C.BrCCCCCCC(OCC)=O.BrCC#CCCCC(OCC)=O.C([O:72][CH:73]([CH2:93][O:94][C:95]1[CH:100]=[CH:99][C:98]([F:101])=[CH:97][CH:96]=1)/[CH:74]=[CH:75]/[CH2:76][N:77]([CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][C:88]([O:90]CC)=[O:89])[S:78]([CH3:81])(=[O:80])=[O:79])(=O)C>>[OH:72][CH:73]([CH2:93][O:94][C:95]1[CH:100]=[CH:99][C:98]([F:101])=[CH:97][CH:96]=1)/[CH:74]=[CH:75]/[CH2:76][N:77]([CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][C:88]([OH:90])=[O:89])[S:78]([CH3:81])(=[O:80])=[O:79]

Participants

6

Reactant 5

HCID 122490Ethyl 7-bromoheptanoateHCID 15174663Ethyl 7-bromohept-5-ynoateHCID 21401585HCID 21401585, compoundHCID 21401637N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamideHCID 21401658ethyl 7-{N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamido}heptanoate

Product 1

HCID 214016247-{N-[4-hydroxy-5-(4-fluorophenoxy)-trans-2-pentenyl]methanesulfonamido}heptanoic acid

Procedure

This compound is prepared by the procedure described in Example 2, Step I, except that N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamide is substituted for the N-[4-acetoxy-5-(4-fluorophenoxy)pentyl]methanesulfonamide and ethyl 7-bromoheptanoate is substituted for ethyl 7-bromo-5-heptynoate. The product is thus ethyl 7-{N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamido}heptanoate. The subsequent hydrolysis (Example 2, Step J) affords the subject compound.

Workup

  1. customThis compound is prepared by the procedure
  2. customThe subsequent hydrolysis (Example 2, Step J)
  3. customaffords the subject compound

Sources & evidence

ORD record
ord-5783abd16efd4e6e9dc67918777c4c8f
Source dataset
uspto-grants-1977_10
Patent number
US04055596

Reaction notes

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