Methanol → 2'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

HRID 1845197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845197
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23]([O:25]C)=[O:24])[CH:11]=1)#[N:2].[OH-].[Li+].CO>O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23]([OH:25])=[O:24])[CH:11]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58188323Methyl 2'-cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

Produkt 1

HCID 581881162'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A round-bottom flask was charged with methyl 2′-cyano-4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate (0.17 g, 0.46 mmol), lithium hydroxide (17 mg, 0.70 mmol), methanol (5 mL), and water (1 mL). The mixture was stirred at room temperature overnight. The evolatiles were removed under reduced pressure and the residue was acidified with 1 N HCl, extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, concentrated to afford the desired product as a white solid. LC-MS: 335.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 8.14 (t, J=1.6 Hz, 1H), 8.10 (t, J=1.5 Hz, 1H), 7.93 (t, J=1.7 Hz, 1H), 7.83 (t, J=0.8 Hz, 1H), 7.66-7.60 (m, 2H), 3.51-3.42 (m, 4H), 2.42 (s, 3H), 1.91-1.83 (m, 4H).

Aufarbeitung

  1. customThe evolatiles were removed under reduced pressure
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d101ee3c4df64e3a92bce2b5592b8252
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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