Hydrochloric Acid → [3-((2R)-2-{[(1R)-1-Phenylethyl]amino}propyl)phenyl]acetic acid

HRID 1866564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866564
[OH-].[Li+].Cl.C[O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C@H:15]([NH:17][C@@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH3:16])[CH:9]=1.Cl>CO>[C:20]1([C@H:18]([NH:17][C@H:15]([CH3:16])[CH2:14][C:10]2[CH:9]=[C:8]([CH2:7][C:6]([OH:26])=[O:5])[CH:13]=[CH:12][CH:11]=2)[CH3:19])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46938908methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride

Produkt 1

HCID 58907418[3-((2R)-2-{[(1R)-1-Phenylethyl]amino}propyl)phenyl]acetic acidAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Lithium hydroxide solution (1M in water, 90 mL, 90 mmol) was added to a solution of methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (preparation 26), (13.5 g, 43.5 mmol) in methanol (200 mL) and the mixture was stirred at room temperature for 18 hours. 1M Hydrochloric acid (90 mL) was then added to the reaction mixture and the methanol removed in vacuo. The resulting precipitate was filtered off and washed with water (20 mL) and a mixture of ethanol/diethyl ether, 20:80, to afford the title compound as a solid in 91% yield, 11.8 g 1H NMR (400 MHz, CD3OD) δ: 7.52-7.45 (5H, m), 7.22-7.18 (2H, m), 7.19 (1H, s), 6.92 (1H, d), 4.56-4.48 (1H, q), 3.46 (2H, s), 3.26-3.13 (2H, m), 2.66-2.62 (1H, m), 1.62 (3H, d), 1.16 (3H, d) ppm; LRMS ESI m/z 298 [M+H]+

Aufarbeitung

  1. customthe methanol removed in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water (20 mL)
  4. additiona mixture of ethanol/diethyl ether, 20:80

Quellen und Nachweise

ORD-Eintrag
ord-06c390cc73a9407485da74ab8b144ecc
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629358B2

Notizen zur Reaktion

Wird geladen…