Potassium Carbonate → HCID 58437190, Verbindung

HRID 40495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40495
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH:15][S:16]([C:19]2[S:20][C:21]([C:24]#[C:25][Si](C)(C)C)=[CH:22][CH:23]=2)(=[O:18])=[O:17])[C:12]([OH:14])=[O:13])=[CH:2]1.C([O-])([O-])=O.[K+].[K+]>ClCCl.CO>[C:24]([C:21]1[S:20][C:19]([S:16]([NH:15][C@H:11]([CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[C:12]([OH:14])=[O:13])(=[O:18])=[O:17])=[CH:23][CH:22]=1)#[CH:25]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 58437200(R)-3-(1H-Indol-3-yl)-2-(5-trimethylsilanylethynyl-thiophene-2-sulfonylamino)-propionic acid

Produkt 1

HCID 58437190HCID 58437190, VerbindungAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of crude (R)-3-(1H-Indol-3-yl)-2-(5-trimethylsilanylethynyl-thiophene-2-sulfonylamino)-propionic acid 8 (0.126 g, 0.282 mmol) in dichloromethane/methanol mixture (1:1, 10 mL) was added K2CO3 (0.047 g, 0.34 mmol) and allowed to stir for 60 minutes. The reaction mixture was then filtered and retentate washed with dichloromethane-methanol mixture. The combined filtrate was concentrated under reduced pressure and then purified using a SAX column to obtain (R)-2-(5-Ethynyl-thiophene-2-sulfonylamino)-3-(1H-indol-3-yl)-propionic acid 9 (52 mg, 49%). LC-MS (ES+) 375; (ES−) 373.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. washretentate washed with dichloromethane-methanol mixture
  3. concentrationThe combined filtrate was concentrated under reduced pressure
  4. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-d1302ec85dcb4435b103bd606b55f371
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530453B2

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