Acetic Acid → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

HRID 465609Notes

Reaction equation

HRID 465609 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH2:20][CH2:21][C:22]([O:24][CH2:25]C)=[O:23])(=[O:13])=[O:12])=[CH:7][CH:6]=1.C(O)(=O)C>CO>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])(=[O:12])=[O:13])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10322927Ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoateHCID 10942334Sodium Methoxide

Product 1

HCID 10479691Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 130.15 g of sodium methoxide in 2.4 l methanol is added at room temperature to a solution of 5469 g of ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate in 52.3 l of methanol. The mixture is stirred for 40 h under nitrogen. Glacial acetic acid (145.5 g) is added and the reaction mixture is evaporated to dryness at 60° and 3 mm Hg (=4.00 mbar). The residue is dissolved in 40 l of ethyl acetate, the solution is washed with dilute sodium bicarbonate solution and then with 5% sodium bisulfite, dried over sodium sulfate, treated with charcoal and evaporated to dryness to yield crude methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate (compound of example 4a).

Workup

  1. customthe reaction mixture is evaporated to dryness at 60°
  2. dissolutionThe residue is dissolved in 40 l of ethyl acetate
  3. washthe solution is washed with dilute sodium bicarbonate solution
  4. dry with materialwith 5% sodium bisulfite, dried over sodium sulfate
  5. additiontreated with charcoal
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-405491b769a443e29962fc1852da3cc7
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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