Acetic Acid → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-hydroxymethyl-2-oxo-2-phenylethyl)amide

HRID 751733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751733
[Si]([O:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]1[NH:31][C:25]2=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=[C:24]2[CH:23]=1)=[O:21])[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1.O>[OH:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]1[NH:31][C:25]2=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=[C:24]2[CH:23]=1)=[O:21])[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 597535505-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide

Produkt 1

HCID 597536965-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-hydroxymethyl-2-oxo-2-phenylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S) -(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide (Preparation 101, 220 mg, 0.48 mmol) in THF (10 mL) was added acetic acid (60 μL) and tetrabutylammonium fluoride solution (1 ml, 1M in THF) at rt. After stirring for 3 h the reaction mixture was distributed between ethyl acetate (100 mL) and water (30 mL). The organic layer was separated, then washed with brine (50 ml), dried (MgSO4) and concentrated to a solid residue. Recrystallisation from THF gave the title compound.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a solid residue
  5. customRecrystallisation from THF

Quellen und Nachweise

ORD-Eintrag
ord-0eedd35946f049bc88156b8759a0742b
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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