Hydrochloric Acid → {4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid

HRID 1685760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685760
C([O:3][C:4](=[O:20])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[NH:19])[NH:17][OH:18])=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.[CH2:21]([N:23]([CH2:26][C:27]1[S:31][C:30]([C:32](O)=O)=[CH:29][C:28]=1[CH3:35])[CH2:24][CH3:25])[CH3:22].Cl>[Li+].[OH-].CO>[CH2:21]([N:23]([CH2:26][C:27]1[S:31][C:30]([C:32]2[O:18][N:17]=[C:16]([C:13]3[CH:12]=[CH:11][C:10]([S:7]([NH:6][CH2:5][C:4]([OH:3])=[O:20])(=[O:8])=[O:9])=[CH:15][CH:14]=3)[N:19]=2)=[CH:29][C:28]=1[CH3:35])[CH2:24][CH3:25])[CH3:22]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178472928HCID 178472928, Verbindung

Produkt 1

HCID 67265676{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acidAusbeute 1,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3939Lithium HydroxideLösungsmittel

Versuchsvorschrift

{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid ethyl ester (98 mg) is obtained starting from [4-(N-hydroxycarbamimidoyl)-benzenesulfonylamino]-acetic acid ethyl ester (233 mg, 0.774 mmol) and 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (160 mg, 0.704 mmol) according to Method A; LC-MS: tR=0.57 min; [M+1]+=493.17. This material (98 mg, 199 μmol) is dissolved in 2 N aq. LiOH (25 mL) and methanol (25 mL). The mixture is stirred at rt for 20 h before it is acidified by adding 1 N aq. HCl and extracted twice with EA. The combined organic extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (6 mg) as a white solid; LC-MS: tR=0.50 min; [M+1]+=465.02.

Aufarbeitung

  1. extractionextracted twice with EA
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-c0d9b36298bd4f348e8a9beccd73de7c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148410B2

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