Acetic Anhydride → 2-acetylamino-N-benzyl-3-difluoromethoxy-propionamide

HRID 601978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601978
[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.[C:25](OC(=O)C)(=[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 7918Acetic AnhydrideHCID 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

2-Amino-N-benzyl-3-difluoromethoxy-propionamide (195 mg, 0.80) was mixed with triethylamine (322 mg, 3.19 mmol) in THF (5 mL). Acetic anhydride (98.5 mg, 0.96 mmol) was then added and the reaction mixture stirred for 1 hour. The mixture was then diluted with ethyl acetate and washed with water. The organic layer was dried and concentrated. The residue was purified by column chromatography using hexanes:ethyl acetate (50:50 to 0:100). The isolated product was triturated with diethyl ether to give 2-acetylamino-N-benzyl-3-difluoromethoxy-propionamide (135 mg, 59%) as a white solid.

Aufarbeitung

  1. washwashed with water
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography
  5. customThe isolated product was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1325913e6578410b96ede0890794d6c4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902401B2

Notizen zur Reaktion

Wird geladen…