Dicyclohexylamine → 1-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)-benzenesulfonyl]amino}cyclopentanecarboxylic acid, dicyclohexylaminium salt

HRID 1953211Notes

Reaction equation

HRID 1953211 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:9]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2].[CH:34]1([NH:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(O)C>[CH:41]1([NH2+:40][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]1.[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[CH:24][CH:25]=1)(=[O:19])=[O:18])[C:9]1([C:14]([O-:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7582DicyclohexylamineHCID 110490941-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}-cyclopentanecarboxylic Acid

Product 1

HCID 1317219831-{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)-benzenesulfonyl]amino}cyclopentanecarboxylic acid, dicyclohexylaminium saltYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.10 g (6.5 mmol) of crude 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid in 30 mL of ethanol was treated with 1.28 mL (6.5 mmol, 1 equivalent) of dicyclohexylamine at ambient temperature producing solids within five minutes. This mixture was stirred at ambient temperature overnight and then at 0° C. for five hours. White solids were isolated by filtration, washed with 10 mL of cold ethanol, and air dried giving 2.89 g (67%) of 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzene sulfonyl]amino}cyclopentanecarboxylic acid, dicyclohexylaminium salt.

Workup

  1. customproducing solids within five minutes
  2. waitat 0° C. for five hours
  3. customWhite solids were isolated by filtration
  4. washwashed with 10 mL of cold ethanol, and air
  5. customdried

Sources & evidence

ORD record
ord-55eaa97b46de4e739342e659e115da62
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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