ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)-amino]-4-[2-(3-pyridyloxy)ethyl]-octanoate → Ethyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]octanoate

HRID 465616Notes

Reaction equation

HRID 465616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:31][CH2:32][O:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])C(OC(C)(C)C)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:31][CH2:32][O:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 14986717ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)-amino]-4-[2-(3-pyridyloxy)ethyl]-octanoate

Product 1

HCID 14986718Ethyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]octanoate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2.9 g (5 mmol) of ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)-amino]-4-[2-(3-pyridyloxy)ethyl]-octanoate in 30 ml trifluoroacetic acid is stirred at room temperature. After 18 h the reaction mixture is evaporated to dryness. The residue is dissolved in methylene chloride and the solution is washed with saturated NaHCO3 solution, dried and evaporated. The residue is chromatographed on silica gel using 1:1 ethyl acetate/methylene chloride as eluent to yield ethyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]-octanoate.

Workup

  1. customAfter 18 h the reaction mixture is evaporated to dryness
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washthe solution is washed with saturated NaHCO3 solution
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on silica gel using 1:1 ethyl acetate/methylene chloride as eluent

Sources & evidence

ORD record
ord-17d331d649a34bbba316fc6e268f8cc9
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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