Benzylamine → 2-(Benzo[b]thiophen-3-yl)-2-(benzylamino)acetic acid

HRID 469478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469478
[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[C:13]1([CH2:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.O=[CH:23][C:24]([OH:26])=[O:25]>C(#N)C>[S:1]1[CH:5]=[C:4]([CH:23]([NH:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:24]([OH:26])=[O:25])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Produkt 1

HCID 585569862-(Benzo[b]thiophen-3-yl)-2-(benzylamino)acetic acidAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of benzo[b]thiophen-3-ylboronic acid (300 mg, 1.68 mmol), phenylmethanamine (184 μl, 1.68 mmol) and 2-oxoacetic acid hydrate (155 mg, 1.68 mmol) in acetonitrile (20 ml) was stirred at room temperature for 2 hours. The solvent was removed and crude was triturated with Et2O/CH3CN (9/1) to obtain 2-(benzo[b]thiophen-3-yl)-2-(benzylamino)acetic acid (303 mg, 60.5% yield).

Aufarbeitung

  1. customThe solvent was removed
  2. customcrude was triturated with Et2O/CH3CN (9/1)

Quellen und Nachweise

ORD-Eintrag
ord-dbd72fbb2af145e6aa11022e16828ef0
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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