Triethylamine → N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamide

HRID 1520510

Reaktionsgleichung

Reaktionsgleichung von HRID 1520510
[NH2:1][C@@H:2]([CH2:14][F:15])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N+:12]=[N-:13])=[CH:7][CH:6]=1)[OH:4].C(N(CC)CC)C.[Cl:23][CH:24]([Cl:30])[C:25](OCC)=[O:26]>CO>[N:11]([C:8]1[CH:7]=[CH:6][C:5]([C@@H:3]([OH:4])[C@H:2]([NH:1][C:25](=[O:26])[CH:24]([Cl:30])[Cl:23])[CH2:14][F:15])=[CH:10][CH:9]=1)=[N+:12]=[N-:13]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10808Ethyl dichloroacetateHCID 86695457(1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol

Produkt 1

HCID 86695459N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamideAusbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To the stirred solution of (1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol (600 mg, 2.83 mmol) in methanol (6.5 mL) is added triethyl amine (0.57 g, 5.64 mmol) and ethyl dichloroacetate (0.88 g, 5.60 mmol). Resulting reaction mixture is stirred under nitrogen at room temperature for 16 hours. Solvent is evaporated in vacuo to get the crude material purified by column chromatography eluting in 0.5% methanol in dichloromethane to afford the title compound (150 mg). 1H-NMR (400 MHz, DMSO-d6) δ: 4.40-4.41 (m, 1H), 4.24-4.26 (m, 0.5H), 4.36-4.38 (m, 0.5H), 4.52-4.54 (m, 0.5H), 4.64-4.66 (m, 0.5H), 4.84 (t, 1H, J=3.64 Hz), 5.96 (d, 1H, J=4.24 Hz), 6.49 (s, 1H), 7.05 (d, 2H, J=8.48 Hz), 7.38 (d, 2H, J=8.44 Hz), 8.58 (d, 1H, J=8.98 Hz). LC-Ms (m/z): [M−H]=318.8.

Aufarbeitung

  1. customResulting
  2. customreaction mixture
  3. customSolvent is evaporated in vacuo
  4. customto get the crude material
  5. custompurified by column chromatography
  6. washeluting in 0.5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-86b644b3b4554488963332b4542c6284
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073894B2

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