2-Bromo-5-ethoxypyridine → (1S,2S)-2-Phenyl-cyclopropanecarboxylic acid [(R)-1-(5-ethoxy-pyrdin-2-yl)-2-hydroxy-ethyl]-amide

HRID 1908687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908687
[OH:1][CH2:2][C@H:3]([NH:14][C:15]([C@H:17]1[CH2:19][C@@H:18]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:4]1C=N[C:7]([O:10][CH2:11][CH2:12]C)=[CH:8][CH:9]=1.[NH2:26][C@H:27](C1C=CC(OCC)=CN=1)CO.BrC1C=CC(OCC)=CN=1>>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C@@H:3]([NH:14][C:15]([C@H:17]2[CH2:19][C@@H:18]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:16])[CH2:2][OH:1])=[N:26][CH:27]=1)[CH3:12]

Komponenten

4

Edukt 3

HCID 234368922-Bromo-5-ethoxypyridineHCID 71201933(1S,2S)-2-Phenyl-cyclopropanecarboxylic acid [(R)-2-hydroxy-1-(6-propoxy-pyridin-3-yl)-ethyl]-amideHCID 86675618(R)-2-Amino-2-(5-ethoxy-pyridin-2-yl)-ethanol

Produkt 1

HCID 71201958(1S,2S)-2-Phenyl-cyclopropanecarboxylic acid [(R)-1-(5-ethoxy-pyrdin-2-yl)-2-hydroxy-ethyl]-amide

Versuchsvorschrift

Prepared analogously to Compound 21 using IM46 and (R)-2-Amino-2-(5-ethoxy-pyridin-2-yl)-ethanol (prepared from commercially available 2-Bromo-5-ethoxy-pyridine CAS 42834-01-5 analogously to IM36). Compound 52 was further purified by SFC (Column: Chiralpack OJ250×30 mm, Mobile phase: Supercrital CO2/MeOH+NH4OH=55/45 at 50 mL/min, column temperature: 38° C., Nozzle Pressure: 100 Bar, Nozzle Temp=60° C., Evaporator temp=20 C, Trimmer temp=25° C., Detector: 220 nm). Yield=163 mg. 1H NMR (CDCl3 400 MHz, TMS): δ 8.15 (d, J=2.8 Hz, 1H), 7.08-7.31 (m, 6H), 7.06 (d, J=7.2 Hz, 2H), 5.11-5.15 (m, 1H), 4.00-4.08 (m, 3H), 3.87-3.90 (m, 1H), 2.47-2.52 (m, 1H), 1.63-1.76 (m, 3H), 1.43 (t, J=7.2 Hz, 3H), 1.27-1.31 (m, 1H); [α]20, D=182.0 (c=0.234 g/100 mL, EtOH)

Aufarbeitung

  1. customCompound 52 was further purified by SFC (Column: Chiralpack OJ250×30 mm, Mobile phase: Supercrital CO2/MeOH+NH4OH=55/45 at 50 mL/min, column temperature: 38° C., Nozzle Pressure: 100 Bar, Nozzle Temp=60° C., Evaporator temp=20 C, Trimmer temp=25° C., Detector: 220 nm)

Quellen und Nachweise

ORD-Eintrag
ord-05f24c091c504bc198c19ebce2bddb55
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598213B2

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