Hydrochloric Acid → N-(Ethoxycarbonyl)-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serine

HRID 1265223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1265223
[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:29]([O:31]C)=[O:30])[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2].[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:29]([OH:31])=[O:30])[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59050114Methyl N-(ethoxycarbonyl)-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate

Produkt 1

HCID 59050116N-(Ethoxycarbonyl)-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The compound of Example 7 (100.0 mg, 0.23 mmol, 1 equiv) was dissolved in THF/MeOH/H2O (3:1:1 2.3 mL) and the solution was cooled to 0° C. followed by addition of solid lithium hydroxide (5.4 mg, 0.23 mmol, 1 equiv). The reaction mixture was allowed to reach rt and stirred for 1 hour. It was acidified with 0.1 M aqueous HCl solution to pH 3 and extracted three times with ethyl acetate. The combined organic extracts were dried over Na2SO4 and the solvents were removed under reduced pressure and the remaining crude product was purified by chromatography (SiO2; toluene/EtOH/AcOH 95:4:1). Yield 23.7 mg, 24.5%. 1H NMR (DMSO; 200 MHz) δ 13.05 (brs, 1H); 8.59 (s, 1H); 7.72 (s, 1H); 7.05 (d, 1H); 7.41-7.22 (m, 3H); 7.17-7.03 (m, 3H); 6.91 (d, 1H); 6.22 (dd, 1H); 4.49-4.81 (m, 1H); 4.30-4.19 (m, 2H); 4.0 (q, 2H); 3.04 (q, 2H); 1.49 (sextett, 2H); 1.19 (t, 3H); 0.94 (t, 3H). MS (EI) 430 (M+H), 345, 210.

Aufarbeitung

  1. customto reach rt
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customthe solvents were removed under reduced pressure
  5. customthe remaining crude product was purified by chromatography (SiO2; toluene/EtOH/AcOH 95:4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3dd022a53fb44f54a03ef1e88a8d0d63
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545029B2

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