Water → HCID 9982645, compound

HRID 1494085Notes

Reaction equation

HRID 1494085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)(C(OCC)=O)[C:19]([O:21]CC)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.C(=O)(O)[O-].[Na+]>Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 14986647HCID 14986647, compound

Product 1

HCID 9982645HCID 9982645, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.4 g of ethyl 8-(p-chlorophenyl-sulfonamido)-2-[5-(3-pyridyl)-pentyl]-2-(ethoxycarbonyl)-octanoate in 50 mL of 6N HCl and 10 mL of acetic acid is heated to reflux for 23 hours after which time it is evaporated to give an oil. This is treated with water, the solution is neutralized with solid sodium bicarbonate to a pH of 6.4 and extracted with ethyl acetate. The ethyl acetate extract is dried over magnesium sulfate, filtered and concentrated to give crude product which is first purified by column chromatography over silica gel using ethyl acetate as eluent, and then further purified by preparative TLC chromatography using ethyl acetate, acetic acid (99.5:0.5) as eluent to give 8-(p-chlorophenylsulfonamido)-2-[5-(3-pyridyl)pentyl]-octanoic acid as an oil, NMR (CDCl3): delta 7.77 (d,2H), 7.4 (d,2H), 2.85 (t,2H), 2.55 (t,2H).

Workup

  1. temperatureto reflux for 23 hours after which time it
  2. customis evaporated
  3. customto give an oil
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialis dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give crude product which
  10. customis first purified by column chromatography over silica gel
  11. customfurther purified by preparative TLC chromatography

Sources & evidence

ORD record
ord-ce472f662aa049df96036edae37bb2f5
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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