Methanesulfonic Acid → (4S,2S)-4-Methanesulfonyloxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methylester
反応式
[S:1]([O-:5])(=[O:4])(=[O:3])[CH3:2].CS(O)(=O)=O.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][O:38][C:39]([C@@H:41]1[CH2:45][C@@H:44](O)[CH2:43][N:42]1[S:47]([C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=1)(=[O:49])=[O:48])=[O:40].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.CCOC(C)=O.CCCCCC.O>[CH3:37][O:38][C:39]([C@@H:41]1[CH2:45][C@H:44]([O:3][S:1]([CH3:2])(=[O:5])=[O:4])[CH2:43][N:42]1[S:47]([C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=1)(=[O:49])=[O:48])=[O:40]参加物
反応物 6
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 80 °C
実験手順
Via Mesylate: A biphasic solution of 13.9 ml (215 mmol) methanesulfonic acid, 29.8 ml (215 mmol) triethylamine and 58.7 g (224 mmol) triphenylphosphine in 150 ml toluene was added to a suspension of 60 g (179 mmol) (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester in 300 ml toluene which was stirred mechanically. After adding 44.9 ml (233 mmol) of diisopropyl azodicaboxylate (exothermic!) the solution was heated for 2.5 h at 80° C. 300 ml water was added at room temperature and extracted with EtOAc (3×300 ml). The organic phase was washed with aqueous 10% KHSO4 (2×100 ml), 10% NaCl (2×150 ml) dried over Na2SO4 and evaporated to give 180 g of crude product. Flash chromatography (EtOAc/hexane 1:1) gave 63.7 g (86%) of (4S,2S)-4-methanesulfonyloxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methylester.
後処理
- extractionextracted with EtOAc (3×300 ml)
- washThe organic phase was washed with aqueous 10% KHSO4 (2×100 ml), 10% NaCl (2×150 ml)
- dry with materialdried over Na2SO4
- customevaporated
- customto give 180 g of crude product
出典と根拠
- ORDレコード
- ord-6fffb98b9ee84509b854a04c00c36d11
- 出典データセット
- uspto-grants-2004_09
- 特許番号
- US06790860B2
反応ノート
読み込み中…