HCID 54535752, compound → HCID 54146484, compound

HRID 1953233Notes

Reaction equation

HRID 1953233 reaction equation
[C:1]([O:5][C:6]([C:8]1([N:13]([CH:31]=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([C:8]1([N:13]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 54535752HCID 54535752, compound

Product 1

HCID 54146484HCID 54146484, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-{(2-Ethoxycarbonyl-vinyl)-[4-(4-fluoro-phenoxy)-benzenesulfonyl]-amino}-cyclopentanecarboxylic acid tert-butyl ester (1.23 g, 2.3 mmole) in 50 mL ethanol with 723 mg 5% Pd/C catalyst was hydrogenated at ambient temperature until HPLC indicated that the reaction was complete. The catalyst was filtered and the filtrate evaporated to give an oil which was submitted to chromatography over silica gel, eluting with 105 ethyl acetate in hexane. 1-{(2-Ethoxycarbonyl-ethyl)-[4-(4-fluoro-phenoxy)-benzenesulfonyl]-amino}-cyclopentanecarboxylic acid tert-butyl ester was isolated as a colorless oil (875 mg, 71% yield). 1H NMR (CDCl3) □ 7.75-7.80 (m, 2H), 6.86-7.01 (m, 6H), 4.09 (q, J=7.2, 2H), 3.44-3.48 (m, 2H), 2.66-2.72, m, 2H), 2.09-2.15 (m, 2H), 1.52-1.74, m, 4H), 1.43 (s, 9H), 1.21 (t, J=7.2 Hz, 3H).

Workup

  1. customwas hydrogenated at ambient temperature until HPLC
  2. filtrationThe catalyst was filtered
  3. customthe filtrate evaporated
  4. customto give an oil which
  5. washeluting with 105 ethyl acetate in hexane

Sources & evidence

ORD record
ord-6263541d835048cb8349932ed4e42776
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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