Trifluoroacetic acid → N-((1S,2R)-2-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-1-fluoromethyl-2-hydroxy-ethyl)-2,2-difluoro-acetamide

HRID 1487497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487497
[NH2:1][CH:2]([C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[O:23]C(C)(C)[N:21]([C:26](=[O:30])[CH:27]([F:29])[F:28])[C@H:20]3[CH2:31][F:32])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][CH:2]([C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C@@H:19]([OH:23])[C@H:20]([NH:21][C:26](=[O:30])[CH:27]([F:29])[F:28])[CH2:31][F:32])=[CH:17][CH:18]=2)=[CH:9][CH:8]=1)[C:3]([F:4])([F:5])[F:6]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866954471-((4R,5R)-5-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanone

Produkt 1

HCID 86695448N-((1S,2R)-2-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-1-fluoromethyl-2-hydroxy-ethyl)-2,2-difluoro-acetamideAusbeute 40,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-((4R,5R)-5-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl)-2,2-difluoro-ethanone (35 mg, 0.076 mmol) in CH2Cl2 (1 mL) is added trifluoroacetic acid (1 mL) at 0° C. then stirred to room temperature for 3 hours. The solvent evaporated in vacuo and the crude material is diluted with ammonia solution and extract with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by preparative TLC using in 70% ethyl acetate in hexane to afford the title compound (0.013 g): 1H-NMR (400 MHz, DMSO-d6) δ: 2.66 (d, J=7.28 Hz, 2H), 4.30-4.36 (m, 1.5H), 4.40-4.44 (m, 0.5H), 4.54-4.55 (m, 0.5H), 4.61-4.68 (m, 1.5H), 4.89 (t, J=3.8 Hz, 1H), 5.93 (d, J=4.36 Hz, 1H), 6.19 (t, J=53.8 Hz, 1H), 7.45 (d, J=8.32 Hz, 2H), 8.00 (d, 1.16 Hz, 2H), 8.05 (d, J=8.28 Hz, 2H), 8.73 (s, 1H), 8.84 (d, J=8.56 Hz, 1H). LC-MS (m/z): [M+H]=422.0.

Aufarbeitung

  1. customThe solvent evaporated in vacuo
  2. additionthe crude material is diluted with ammonia solution
  3. extractionextract with ethyl acetate
  4. dry with materialOrganic layer is dried over sodium sulphate, solvent
  5. customis evaporated in vacuo
  6. custompurified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-dfeac133eb9947e2852a29beb50815eb
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428528B2

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