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

HRID 1730133Notes

Reaction equation

HRID 1730133 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-aa5b54aca5954e83b0dd111596b5d881
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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