StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Glycine methyl ester hydrochloride → Methyl 2-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)acetate

HRID 2175238
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2175238
[C:1](=O)([O:34]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH2:12][CH2:13][CH2:14][N:15]3[C:20](=[O:33])[CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=2[CH3:32])=[CH:6][CH:5]=1.Cl.[NH2:46][CH2:47][C:48]([O:50][CH3:51])=[O:49]>C(Cl)Cl>[CH3:32][C:26]1[C:27]([CH3:31])=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][CH2:23][CH2:22][CH2:21][C:20]([N:15]1[C:16]2[C:11](=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:3][O:2][C:1]([NH:46][CH2:47][C:48]([O:50][CH3:51])=[O:49])=[O:34])=[CH:9][CH:8]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]1)=[O:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 122755Glycine methyl ester hydrochlorideHCID 867125814-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyl 4-nitrophenyl carbonate

Produkt 1

HCID 70982580Methyl 2-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)acetateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyl 4-nitrophenyl carbonate (0.020 g, 0.034 mmol), methyl 2-aminoacetate hydrochloride (5.07 mg, 0.040 mmol) and TEA (9.38 μL, 0.067 mmol) in DCM (0.200 mL) was stirred at room temperature for 16 h. After this time, the reaction mixture was quenched with 1 N NaOH. The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The resulting residue was purified by preparative HPLC (PHENOMENEX® Axia Luna column, 5μ, C18, 30×100 mm; 10 min gradient from 75% A:25% B to 0% A:100% B (A=90% H2O/10% MeOH+0.1% TFA); (B=90% MeOH/10% H2O+0.1% TFA); detection at 220 nm) to afford the title compound (11.6 mg, 63% yield) as a clear colorless oil. LCMS, [M+H]+=545.2. 1H NMR (400 MHz, MeOD) δ 7.37 (d, J=7.9 Hz, 2H), 7.25 (d, J=7.4 Hz, 2H), 7.13 (d, J=7.5 Hz, 1H), 7.09 (d, J=6.8 Hz, 2H), 6.98 (t, J=7.9 Hz, 1H), 6.72 (d, J=7.5 Hz, 1H), 6.66 (d, J=8.1 Hz, 1H), 5.14 (s, 2H), 3.87 (s, 3H), 3.79-3.63 (m, 6H), 2.82 (t, J=6.9 Hz, 2H), 2.35 (s, 2H), 2.20-2.04 (m, 5H), 1.87-1.66 (m, 5H).

Aufarbeitung

  1. customAfter this time, the reaction mixture was quenched with 1 N NaOH
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by preparative HPLC (PHENOMENEX® Axia Luna column
  7. custom10 min gradient

Quellen und Nachweise

ORD-Eintrag
ord-09e0ef49eaa44f388f279b425694bdd9
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09062028B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion