Lithium Hydroxide → HCID 86707796, Verbindung

HRID 2174382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174382
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:19][C:18]([C:24]4[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=4)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=3)=[CH:11][CH:10]=2)[CH2:6]1)=[O:4].[OH-].[Li+]>C1COCC1.CO.O>[Cl:32][C:26]1[CH:25]=[C:24]([C:18]2([C:20]([F:21])([F:23])[F:22])[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([N:7]4[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]4)=[CH:10][CH:11]=3)[CH2:19]2)[CH:29]=[C:28]([Cl:30])[C:27]=1[Cl:31]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 86707795HCID 86707795, Verbindung

Produkt 1

HCID 86707796HCID 86707796, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a stirred suspension of 1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid methyl ester (Preparation 11, 1.91 g, 3.77 mmol) in THF:MeOH:H2O (1:1:1, 60 mL) was added lithium hydroxide (0.791 g, 18.87 mmol) at room temperature and stirred at room temperature for 24 hours. After consumption of starting material, reaction mixture was concentrated in vacuo; suspension was diluted with water (20 mL) and acidified with 1N HCl up to pH ˜4. Acidified aqueous layer was extracted with ethyl acetate (5×50 mL). Combined organic layer washed with brine (150 mL), dried over sodium sulphate and evaporated under reduced pressure to afford yellow semi solid, which was triturated with chloroform:n-pentane (1:9) to afford yellow solid (1.57 g, 85%). 1H NMR (400 MHz, DMSO) δ: 3.49-3.52 (m, 1H), 3.90 (t, 2H, J=6.7 Hz), 4.04 (t, 2H, J=8.12 Hz), 4.13-4.25 (m, 2H), 6.46 (d, 2H, J=8.64 Hz), 7.48 (d, 2H, J=8.6 Hz), 7.79 (s, 2H); LC-MS (M+H): =492.60.

Aufarbeitung

  1. customAfter consumption of starting material, reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionsuspension was diluted with water (20 mL)
  4. extractionAcidified aqueous layer was extracted with ethyl acetate (5×50 mL)
  5. washCombined organic layer washed with brine (150 mL)
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customto afford yellow semi solid, which
  9. customwas triturated with chloroform:n-pentane (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-1ddd6853d14d4e90b082c070d5711043
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061013B2

Notizen zur Reaktion

Wird geladen…