Hydrochloric Acid → [4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic Acid

HRID 18497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18497
C([O:3][C:4](=[O:20])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:19])C.[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.II.[OH-].[Na+].Cl>CN(C=O)C.O>[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8]([S:27][C:24]1[CH:23]=[CH:22][C:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][CH:25]=1)=[C:7]([CH3:19])[N:6]2[CH2:5][C:4]([OH:3])=[O:20])(=[O:18])[CH3:17]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14798Sodium HydroxideHCID 27604144-Phenylbenzene-1-thiolHCID 59431286Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

Produkt 1

HCID 24850440[4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic AcidAusbeute 37,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (4-acetylamino-2-methyl-indol-1-yl)-acetic acid ethyl ester (0.27 g) and biphenyl-4-thiol (0.19 g) in DMF (5 ml) was added iodine (0.25 g). After stirring at RT overnight 1M NaOH (3 ml) was added and the reaction stirred at RT for a further 12 hours. The reaction was poured into water, the pH adjusted to 3 using 1M HCl and the organics extracted with EtOAc. The EtOAc extractions were combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give crude material. Purification using RPHPLC gave the title compound as a pink solid (0.16 g).

Aufarbeitung

  1. additionwas added
  2. extractionthe organics extracted with EtOAc
  3. extractionThe EtOAc extractions
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give crude material
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-01bbb7a7e0ec4ddea8d8826b83d044c8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741360B2

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