反応式
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][C@@H:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6].[N:19]([O-])=[O:20].[Na+].O>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:19]=[O:20])[C:5]([NH:7][C@@H:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6]参加物
実験手順
A solution of 0.60 g of 1-(2-chloroethyl)-3-(β-D-glucopyranosyl)urea in 15 ml of 99% formic acid was admixed with 282 mg of sodium nitrite under ice-cooling and stirring. The mixture was stirred for 1 hour under ice-cooling to effect the nitrosation. The reaction mixture, after addition of 15 ml of cold water thereto, was ice-cooled for 30 minutes and then treated with 5 ml of Amberlite IR-120 (H+ form) for the removal of sodium cation. The reaction mixture so treated was concentrated to dryness below 30° C by distilling off the solvent under a reduced pressure. The residue was taken up into a small volume of n-propanol and the solution was admixed with a volume of petroleum ether to give precipitate. The precipitate which deposited was collected by filtration and then dried in a desiccator under vacuum, affording 0.65 g of the titled compound as an amorphous solid of pale yellow color. Yield 92%. mp. 85° C (decomposition). [α]D6 -14° (c 0.5, methanol).
後処理
- temperaturecooling
- stirringThe mixture was stirred for 1 hour under ice-
- temperaturecooling
- temperaturecooled for 30 minutes
- additionThe reaction mixture so treated
- concentrationwas concentrated to dryness below 30° C
- distillationby distilling off the solvent under a reduced pressure
- customto give precipitate
- filtrationThe precipitate which deposited was collected by filtration
- customdried in a desiccator under vacuum
出典と根拠
- ORDレコード
- ord-2b7d926b17e1424d94ab8f606d8f1622
- 出典データセット
- uspto-grants-1978_04
- 特許番号
- US04086415
関連ノート
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