Hydrochloric Acid → HCID 57539219, Verbindung

HRID 601960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601960
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]([CH2:14][O:15][CH:16]([F:18])[F:17])[C:10]([O:12]C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1.C(OCC)(=O)C>[CH2:19]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]([CH2:14][O:15][CH:16]([F:18])[F:17])[C:10]([OH:12])=[O:11])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57539220HCID 57539220, Verbindung

Produkt 1

HCID 57539219HCID 57539219, VerbindungAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 2-dibenzylamino-3-difluoromethoxy-propionate (1.2 g, 3.43 mmol) was stirred with 1N LiOH (10.3 mL, 10.3 mmol) in THF (40 mL) at 50° C. for 2 hours and then stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and acidified with 1N HCl. The organic layer was dried with sodium sulfate and concentrated with silica gel. The product was purified by column chromatography, eluting with 10-50% ethyl acetate in hexanes, to give 2-(dibenzylamino)-3-(difluoromethoxy)propanoic acid (730 mg, 63.5%) as a white solid. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.26-7.42 (m, 10H), 6.29 (bt, 1H), 4.45 (dd, 1H), 4.28 (dd, 1H), 3.94 (q, 4H) and 3.85 (m, 1H).

Aufarbeitung

  1. dry with materialThe organic layer was dried with sodium sulfate
  2. concentrationconcentrated with silica gel
  3. customThe product was purified by column chromatography
  4. washeluting with 10-50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1a3574d6a6a940078754b7ab80759eed
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902401B2

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