反応式
[Si:1]([O:8][C@H:9]([CH2:27][O:28][Si](C(C)(C)C)(C)C)[C@@H:10]([NH:20][S@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([Cl:19])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.C1C=CN=CC=1.F>C1COCC1>[Si:1]([O:8][C@H:9]([CH2:27][OH:28])[C@@H:10]([NH:20][S@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([Cl:19])[CH:13]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
To a 50 mL polypropylene bottle containing (S)—N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide (350.00 mg, 618 μmol) was added THF (10 mL ) and the mixture was allowed to stir at 0° C. for 5 minutes. At this time, PYRIDINE (2699 μl, 33371 μmol) was added via syringe before the addition of HF-Pyridine, 70% HF 30% pyr (1782 μl, 19775 μmol) via a syringe. The reaction was allowed to stir at this temp for 2 h and then quenched by pouring into sodium bicarbonate (sat 150 ml). The aq. layer was extracted with EtOAc 94×75 mL). The combined organics were washed with HCl (0.1 N, 3×100 mL), bicarbonate (sat, 100 mL), brine and dried with sodium sulfate. The dried solution was filtered and concentrated to give a yellow oil which was purified on a 40 g ISCO column to give the title compound.
後処理
- stirringto stir at this temp for 2 h
- customquenched
- additionby pouring into sodium bicarbonate (sat 150 ml)
- extractionThe aq. layer was extracted with EtOAc 94×75 mL)
- washThe combined organics were washed with HCl (0.1 N, 3×100 mL), bicarbonate (sat, 100 mL), brine
- dry with materialdried with sodium sulfate
- filtrationThe dried solution was filtered
- concentrationconcentrated
- customto give a yellow oil which
- customwas purified on a 40 g ISCO column
出典と根拠
- ORDレコード
- ord-2133c55f16114c7a9a8c4b048ffd631b
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07745484B2
関連ノート
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