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

HRID 1953210Notes

Reaction equation

HRID 1953210 reaction equation
C([O:8][C:9]([C:11]1([N:16]([CH:34]=[CH:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.[H][H]>C(O)C.O>[CH2:39]([O:38][C:36]([CH2:35][CH2:34][N:16]([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:11]1([C:9]([OH:10])=[O:8])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:37])[CH3:40]

Participants

5

Reactant 2

HCID 543914121-{(2-Ethoxycarbonylvinyl)-[4-(4-fluorophenoxy) benzenesulfonyl]-amino}cyclopentanecarboxylic Acid Benzyl EsterHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.50 g (4.4 mmol) of 1-{(2-ethoxycarbonylvinyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid benzyl ester in 25 mL of ethanol was treated with 2.5 g of 50% water wet 10% palladium on carbon catalyst and shaken under 53 psi of hydrogen for 21 hours. The catalyst was removed by filtration and washed with ethanol (4×25 mL). The filtrate and washings were combined and concentrated under vacuum to 1.74 g (82%) of crude 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid as a viscous oil.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol (4×25 mL)
  3. concentrationconcentrated under vacuum to 1.74 g (82%) of crude 1-{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid as a viscous oil

Sources & evidence

ORD record
ord-9f36b34a0b13434a80ca87c90ff6b7f7
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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