Hydrochloric Acid → 1-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}-cyclopentanecarboxylic Acid

HRID 1976906Notes

Reaction equation

HRID 1976906 reaction equation
C1([NH2+]C2CCCCC2)CCCCC1.[CH2:14]([O:16][C:17]([CH2:19][CH2:20][N:21]([S:30]([C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[CH:35][CH:34]=1)(=[O:32])=[O:31])[C:22]1([C:27]([O-:29])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:18])[CH3:15].Cl>ClCCl>[CH2:14]([O:16][C:17]([CH2:19][CH2:20][N:21]([S:30]([C:33]1[CH:34]=[CH:35][C:36]([O:39][C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)=[CH:37][CH:38]=1)(=[O:32])=[O:31])[C:22]1([C:27]([OH:29])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:18])[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317219831-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)-benzenesulfonyl]amino}cyclopentanecarboxylic acid, dicyclohexylaminium salt

Product 1

HCID 110490941-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}-cyclopentanecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g (4.5 mmol) of 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid, dicyclohexylaminium salt in 30 mL of dichloromethane was treated with 30 mL of 2N hydrochloric acid at ambient temperature causing immediate precipitation of solids. This mixture was stirred at ambient temperature for three hours. The solids were filtered, the aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with water, dried over sodium sulfate, and concentrated under vacuum to 2.2 g (100%) of 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid as a clear oil.

Workup

  1. customprecipitation of solids
  2. filtrationThe solids were filtered
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum to 2.2 g (100%) of 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid as a clear oil

Sources & evidence

ORD record
ord-58503d7180fb415f9359ec76a713ebef
Source dataset
uspto-grants-2001_05
Patent number
US06229025B1

Reaction notes

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