Acetaldehyde → 2-acetylamino-N-benzyl-3-difluoromethoxy-propionamide

HRID 601965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601965
[NH2:1][CH:2]([CH2:13][O:14][CH:15]([F:17])[F:16])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[CH:25](=[O:27])[CH3:26]>C1COCC1.C(OCC)(=O)C>[C:25]([NH:1][CH:2]([CH2:13][O:14][CH:15]([F:16])[F:17])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])(=[O:27])[CH3:26]

Komponenten

6

Edukt 3

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 23649017HCID 23649017, Verbindung

Produkt 1

HCID 236490162-acetylamino-N-benzyl-3-difluoromethoxy-propionamideAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-N-benzyl-3-(difluoromethoxy)propanamide (195 mg, 0.798 mmol) and triethylamine (322 mg, 3.19 mmol) in THF (5 mL), acetic hydride (98.5 mg, 0.958 mmol) was added. The reaction mixture was stirred at room temperature for an hour, diluted with ethyl acetate and washed with water. The organic layer was concentrated with silica gel and purified by column chromatography, eluting with 50-100% ethyl acetate in hexanes. The product was triturated with diethyl ether to give 2-(acetylamino)-N-benzyl-3-(difluoromethoxy)propanamide (135 mg, 59%) as a white solid, MP: 173.3° C. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.25-7.39 (m, 5H), 6.68 (w, 1H), 6.42 (d, 1H), 6.24 (wt, 1H), 4.73 (m, 1H), 4.48 (d, 2H), 4.24 (dd, 1H), 4.01 (dd, 1H) and 2.05 (s, 3H).

Aufarbeitung

  1. washwashed with water
  2. concentrationThe organic layer was concentrated with silica gel
  3. custompurified by column chromatography
  4. washeluting with 50-100% ethyl acetate in hexanes
  5. customThe product was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-73e0fed07d03485c9c9c0f3e58941a6c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902401B2

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