反応式
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[C:15]([CH3:16])=[C:14](F)[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].Cl.[NH2:19][C@H:20]([C@H:24]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]([F:28])([F:27])[F:26])[C:21]([OH:23])=[O:22]>CS(C)=O>[CH2:30]([O:29][C@H:24]([C:25]([F:26])([F:28])[F:27])[C@@H:20]([NH:19][C:14]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([Cl:7])[C:15]=1[CH3:16])[C:21]([OH:23])=[O:22])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 80 °C
実験手順
Cs2CO3 (3.5 g, 10.7 mmol) was added to a mixture of 2-chloro-4-fluoro-3-methylbenzonitrile (0.79 g, 4.65 mmol) and (2R,3S)-2-amino-3-(benzyloxy)-4,4,4-trifluorobutanoic acid hydrochloride salt (0.93 g, 3.1 mmol) in DMSO (18 mL) at room temperature. The resulting mixture was heated to 80° C. and stirred for 2 days. After cooling to room temperature, the reaction mixture was poured into ice-water (150 mL) and extracted with 10% EtOAc in hexanes (2×50 mL). The aqueous phase was acidified to pH=2˜3 with 2N HCl and extracted with EtOAc (2×100 mL). The EtOAc extracts were washed with water, brine and dried over Na2SO4. Removal of the solvent gave a residue, which was purified by flash chromatography to afford the crude (2R,3S)-3-(benzyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)-4,4,4-trifluorobutanoic acid (280 mg) as a mixture.
後処理
- temperatureAfter cooling to room temperature
- extractionextracted with 10% EtOAc in hexanes (2×50 mL)
- extractionextracted with EtOAc (2×100 mL)
- washThe EtOAc extracts were washed with water, brine
- dry with materialdried over Na2SO4
- customRemoval of the solvent
- customgave a residue, which
- customwas purified by flash chromatography
出典と根拠
- ORDレコード
- ord-af8f8552c7d84365befb26fde6f32dcd
- 出典データセット
- uspto-grants-2014_02
- 特許番号
- US08642632B2
関連ノート
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