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 1520496ノート

反応式

HRID 1520496 の反応式
[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]

参加物

4

反応物 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

生成物 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-acetamide収率 40.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9545c62639d74750bd491a8c15094289
出典データセット
uspto-grants-2015_07
特許番号
US09073894B2

反応ノート

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