Iodoethane → 1{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentane carboxylic acid benzyl ester

HRID 323801

Reaktionsgleichung

Reaktionsgleichung von HRID 323801
[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:34][CH2:35][C:36]([OH:38])=[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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:45](I)[CH3:46]>CN(C)C=O>[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:34][CH2:35][C:36]([O:38][CH2:45][CH3:46])=[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:18])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 155242811{(2-Carboxyethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid benzyl ester

Produkt 1

HCID 155242821{(2-Ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentane carboxylic acid benzyl esterAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1{(2-carboxyethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid benzyl ester (147 grams) in N,N-dimethyl formamide (3 L) at room temperature was added potassium carbonate (150 grams, 1.08 mole) and ethyl iodide (32.4 mL, 0.405 mole). The mixture was stirred for 16 hours at room temperature. After filtration, most of the solvent was removed under vacuum. The residue was taken up in water and acidified using 6N aqueous hydrogen chloride solution. The resulting mixture was extracted with diethyl ether. The organic extract was washed with water and brine, dried over magnesium sulfate, and concentrated to yield 1{(2-ethoxycarbonylethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentane carboxylic acid benzyl ester as a yellow semi-solid (149.1 grams, 96%).

Aufarbeitung

  1. filtrationAfter filtration
  2. custommost of the solvent was removed under vacuum
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e3fe7c3176904c70b78ab13ec6fe6275
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214872B1

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