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 1494155Notes

Reaction equation

HRID 1494155 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-chloro- phenylsulfonyl)-N-(t-butoxycarbonyl)amino]-4-[2-(3-pyridyl- oxy)-ethyl]octanoate in 30 ml trifluoroacetic acid is stirred at room temperature. After 18 hours 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 hours 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-fd6ff43dba7d4972b3e7ea5bde113f5e
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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