Tetrahydrofuran → HCID 22135205, Verbindung

HRID 1826862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1826862
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].O.[OH-].[Li+].[CH2:21]1COCC1>O.Cl>[CH3:21][CH:9]1[CH2:10][CH2:11][CH2:12][C:8]1([C:6](=[O:7])[NH:5][CH2:4][CH2:3][CH:2]([CH3:17])[CH3:1])[C:13]([OH:15])=[O:14]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 22135199HCID 22135199, Verbindung

Produkt 1

HCID 22135205HCID 22135205, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-[N-(3-methylbutyl)carbamoyl]cyclopentanecarboxylate (820 mg, 3.4 mmol) in 25 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (260 mg, 6.12 mmol) in 5.0 mL of water. The reaction mixture was stirred at rt for 16 h. THF was removed under reduced pressure to give a yellow oil which was diluted with 10 mL of 1N HCl. The aqueous phase was extracted with CH2Cl2 (8×15 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford 700 mg (90%) of methyl 1-[N-(3-methylbutyl)carbamoyl]-cyclopentanecarboxylic acid as a white solid. MS [M+H]+ 228.

Aufarbeitung

  1. customTHF was removed under reduced pressure
  2. customto give a yellow oil which
  3. extractionThe aqueous phase was extracted with CH2Cl2 (8×15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ae0138f929f64891bcb8dd777075a081
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053081B2

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