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

Methanol → 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid

HRID 600552
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600552
[N:1]1([C:5]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@H:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])[CH:23]=3)[C:17]([O:19]C)=[O:18])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Li+].O>C1COCC1>[N:1]1([C:5]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@H:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])[CH:23]=3)[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59761163Methyl 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate2×

Produkt 1

HCID 597611453-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acidAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 31) (439 mg, 1.0 mmol) was dissolved in THF (6 mL) and methanol, (2 mL) and 1 N lithium hydroxide (1.24 mL) was added. Water (8 mL) was then added dropwise and the resultant solution stirred for 1 hour at room temperature. The majority of the organic solvents were removed by distillation under reduced pressure. The aqueous residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with water (10 mL) and brine (20 mL), dried (MgSO4) and evaporated under reduced pressure to afford the product (406 mg, 96%). 1H NMR δ (300 MHz, CDCl3) 2.10-2.26 (m, 2H), 2.29-2.43 (m, 2H), 2.55-2.69 (m, 1H), 2.96 (s, 3H), 3.36-3.59 (m, 4H), 4.26 (t, 2H), 4.71 (t, 2H), 4.98 (t, 1H), 6.95 (s, 1H), 7.29 (s, 3H), 7.34 (d, 2H), 7.55 (s, 1H), 8.09 (d, 1H), 8.30 (s, 1H); m/z 411 (M+H)+.

Aufarbeitung

  1. customThe majority of the organic solvents were removed by distillation under reduced pressure
  2. extractionextracted with ethyl acetate (2×40 mL)
  3. washThe combined organic extracts were washed with water (10 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-43cecfa6902b4a7c9ae761f30d38a9eb
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902200B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion