Ethyl 7-bromoheptanoate → 7-{N-[4-hydroxy-5-(4-fluorophenoxy)-2-pentynyl]methanesulfonamido}heptanoic Acid

HRID 1730128Notes

Reaction equation

HRID 1730128 reaction equation
C([O:4][CH:5]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:6]#[C:7][CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11])(=O)C.C(OC(COC1C=CC(F)=CC=1)CCCNS(C)(=O)=O)(=O)C.Br[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]([O:54]CC)=[O:53].BrCC#CCCCC(OCC)=O>>[OH:4][CH:5]([CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[C:6]#[C:7][CH2:8][N:9]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]([OH:54])=[O:53])[S:10]([CH3:13])(=[O:11])=[O:12]

Participants

5

Reactant 4

HCID 122490Ethyl 7-bromoheptanoateHCID 15174663Ethyl 7-bromohept-5-ynoateHCID 21401584N-[4-acetoxy-5-(4-fluorophenoxy)-2-pentynyl]methanesulfonamideHCID 21401585HCID 21401585, compound

Product 1

HCID 214015787-{N-[4-hydroxy-5-(4-fluorophenoxy)-2-pentynyl]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)- 2-pentynyl]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)-2-pentynyl]methanesulfonamide} -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-3ce367539afe4eb78136e1b9ac559d95
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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