Triethylamine → N-p-methoxybenzyl-N-tert.-butylthiomethyl-2-(S)-bromo-3-(R)-hydroxybutyramide
反応式
[Cl-].[CH3:2][O:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][NH2+:9][CH2:10][S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.[Br:40][C@@H:41]([C@H:45]([OH:47])[CH3:46])[C:42](O)=[O:43]>>[CH3:2][O:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]([CH2:10][S:11][C:12]([CH3:14])([CH3:13])[CH3:15])[C:42](=[O:43])[C@@H:41]([Br:40])[C@H:45]([OH:47])[CH3:46])=[CH:6][CH:5]=1参加物
実験手順
In succession, 2.76 g (10 mmol) of p-methoxybenzyl-tert.-butylthiomethylammonium chloride (Example 24), 2.06 g (10 mmol) of dicyclohexyl carbodiimide and, dropwise, 1.40 ml (10 mmol) of triethylamine are added at room temperature to a solution of 1.83 g (10 mmol) of 2-(S)-bromo-3-(R)-hydroxybutyric acid prepared analogously to a method of Shimohigashi Y. et al., Bull. Chem. Soc. Japan 52, 949 (1979). The resulting reaction mixture is stirred at room temperature for 2 hours. The dicyclohexylurea that has precipitated is filtered off with suction and the filtrate is diluted with methylene chloride and washed with water and phosphate buffer solution having a pH of 8. The organic phase is dried over sodium sulphate and concentrated by evaporation and the oily residue is chromatographed over silica gel using toluene/ethyl acetate. The title compound is obtained in the form of a colourless, viscous oil.
後処理
- customprepared analogously to a method of Shimohigashi Y
- customThe resulting reaction mixture
- customThe dicyclohexylurea that has precipitated
- filtrationis filtered off with suction
- additionthe filtrate is diluted with methylene chloride
- washwashed with water and phosphate buffer solution
- dry with materialThe organic phase is dried over sodium sulphate
- concentrationconcentrated by evaporation
- customthe oily residue is chromatographed over silica gel
出典と根拠
- ORDレコード
- ord-1de57efd666a4df18f058051071bcbfc
- 出典データセット
- uspto-grants-1986_09
- 特許番号
- US04614614
反応ノート
読み込み中…