HCID 21401585, compound → 7-{N-[4-hydroxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamido}hept-5-ynoic acid

HRID 1730134Notes

Reaction equation

HRID 1730134 reaction equation
C(OC(COC1C=CC(F)=CC=1)CCCNS(C)(=O)=O)(=O)C.C(OC(COC1C=CC(F)=CC=1)/C=C/CNS(C)(=O)=O)(=O)C.C([O:48][CH:49]([CH2:68][O:69][C:70]1[CH:75]=[CH:74][C:73]([F:76])=[CH:72][CH:71]=1)/[CH:50]=[CH:51]/[CH2:52][N:53]([CH2:58][C:59]#[C:60][CH2:61][CH2:62][CH2:63][C:64]([O:66]C)=[O:65])[S:54]([CH3:57])(=[O:56])=[O:55])(=O)C>>[OH:48][CH:49]([CH2:68][O:69][C:70]1[CH:71]=[CH:72][C:73]([F:76])=[CH:74][CH:75]=1)/[CH:50]=[CH:51]/[CH2:52][N:53]([CH2:58][C:59]#[C:60][CH2:61][CH2:62][CH2:63][C:64]([OH:66])=[O:65])[S:54]([CH3:57])(=[O:56])=[O:55]

Participants

4

Reactant 3

HCID 21401585HCID 21401585, compoundHCID 21401617methyl 7-{N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl]-methanesulfonamido}hept-5-ynoateHCID 21401637N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamide

Product 1

HCID 214991037-{N-[4-hydroxy-5-(4-fluorophenoxy)trans-2-pentenyl]methanesulfonamido}hept-5-ynoic acid

Procedure

This compound is prepared by the procedure described in Example 2, Step I, except that the N-[4 -acetoxy-5-(4-fluorophenoxy)pentyl]methanesulfonamide is replaced by an equimolar amount of N-[4-acetoxy-5-(4 -fluorophenoxy)trans-2-pentenyl]methanesulfonamide (Example 6, Step G). This product is thus methyl 7-{N-[4-acetoxy-5-(4-fluorophenoxy)trans-2-pentenyl] -methanesulfonamido}hept-5-ynoate. The subsequent hydrolysis is carried out as described in Example 2, Step J and affords 7-{N-[4-hydroxy-5-(4-fluorophenoxy)trans-2 -pentenyl]methanesulfonamido}hept-5-ynoic acid. The hydrogenation is carried out by the procedure described in Example 3 and affords the subject compound.

Workup

  1. customThis compound is prepared by the procedure
  2. customThe subsequent hydrolysis

Sources & evidence

ORD record
ord-3237767bfca1433b99718181a46a0c10
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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