Water → HCID 58883455, Verbindung

HRID 2377447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377447
[CH:1]([O:4][C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=[O:22])=[C:16]([F:25])[CH:15]=2)=[CH:8][C:7]=1[CH2:26][N:27]([CH:29]1[CH2:31][CH2:30]1)[CH3:28])([CH3:3])[CH3:2].O1CCCC1.O.O.[OH-].[Li+]>CO>[CH:1]([O:4][C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[C:16]([F:25])[CH:15]=2)=[CH:8][C:7]=1[CH2:26][N:27]([CH:29]1[CH2:31][CH2:30]1)[CH3:28])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 690779862-[(Cyclopropyl-methyl-amino)-methyl]-4-(3-fluoro-4-methoxycarbonylmethyl-phenylethynyl)-benzoic acid isopropyl ester2×

Produkt 1

HCID 58883455HCID 58883455, VerbindungAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2-[(cyclopropyl-methyl-amino)-methyl]-4-(3-fluoro-4-methoxycarbonylmethyl-phenylethynyl)-benzoic acid isopropyl ester (Intermediate 124, 0.04 g, 0.09 mmol) in a mixture of methanol (2 mL), tetrahydrofuran (2 mL) and water (1 mL) was treated with lithium hydroxide monohydrate (0.042 g, 1 mmol) and the resulting reaction mixture was stirred at ambient temperature for 2 h. The volatiles were evaporated in vacuo, the residue was neutralized with saturated, aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a solid. Preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase afforded the title product as a white solid (0.026 g, 54%). 1H NMR (300 MHz, CDCl3): δ 7.71 (d, 1H, J=8.1 Hz), 7.64 (s, 1H), 7.41 (d, 1H, J=8.1 Hz), 7.17-7.09 (m, 3H), 5.20 (heptet, 1H, J=6.3 Hz), 4.16 (s, 2H), 3.54 (s, 2H), 2.34 (s, 3H), 1.91 (m, 1H), 1.36 (d, 6H, J=6.3 Hz), 0.50-0.41 (m, 4H).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a solid

Quellen und Nachweise

ORD-Eintrag
ord-3f072d0d972b46ac9697e986402f0c59
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468391B2

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