Triethylamine → HCID 57539227, Verbindung

HRID 601962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601962
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:9]([CH2:13][O:14][CH:15]([F:17])[F:16])[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH2:46])=[CH:43][CH:42]=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:9]([CH2:13][O:14][CH:15]([F:16])[F:17])[C:10]([NH:46][CH2:45][C:44]1[CH:47]=[CH:48][C:41]([F:40])=[CH:42][CH:43]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 673264-FluorobenzylamineHCID 57539219HCID 57539219, Verbindung

Produkt 1

HCID 57539227HCID 57539227, VerbindungAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(dibenzylamino)-3-(difluoromethoxy)propanoic acid (335.4 mg, 1 mmol) and triethylamine (404.8 mg, 4 mmol) in THF (5 mL) at −5° C., isobutyl chloroformate (143.5 mg, 1.05 mmol) was added dropwise. After 20 minutes, 4-fluorobenzylamine (137.5 mg, 1.1 mmol) was added and the reaction mixture allowed to warm up to room temperature. The mixture then was diluted with ethyl acetate and washed with water, 0.5 N HCl and Brine. The organic layer was dried over magnesium sulphate, concentrated with silica gel and purified by column chromatography, eluting with 10˜20% ethyl acetate in hexanes, to give 2-dibenzylamino-3-difluoromethoxy-N-(4-fluorobenzyl)propionamide (395 mg, 89.2%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.56 (t, 1H), 6.98-7.32 (m, 14H), 6.35 (wt, 1H), 4.61 (dd, 1H), 4.41 (m, 3H), 3.86 (d, 2H), 3.70 (d, 2H) and 3.68 (m, 1H).

Aufarbeitung

  1. washwashed with water, 0.5 N HCl and Brine
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. concentrationconcentrated with silica gel
  4. custompurified by column chromatography
  5. washeluting with 10˜20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ef216c0586494acfa8c75469e41cfd2b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902401B2

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