Water → N-Acryloyl-D-glucamine

HRID 374406

反応式

HRID 374406 の反応式
[NH2:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].N([CH2:16][CH2:17][CH:18]=[C:19]([CH3:23])[C:20]([O-])=[O:21])=C=O.[N-:24]=[C:25]=[O:26].[OH2:27]>>[C:25]([NH:24][C@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:27])[OH:4])[OH:6])[OH:8])[CH:11]=[O:12])(=[O:26])[C:17]([CH3:18])=[CH2:16].[C:20]([NH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])(=[O:21])[CH:19]=[CH2:18].[C:20]([NH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])(=[O:21])[C:19]([CH3:23])=[CH2:18]

参加物

7

反応物 4

HCID 962WaterHCID 105034IsocyanateHCID 452501GlucamineHCID 76540206Isocyanatoethyl-methylacrylate

生成物 3

HCID 18639241N-Acryloyl-D-glucamineHCID 186497851-Deoxy-1-methacrylamido-glucitolHCID 227925012-Deoxy-2-methacrylamido-D-glucose

反応条件

温度
-3 °C

実験手順

20 g 1-amino-1-deoxyglucitol (1a) are dissolved according to the method of Klein et al. (S. Engelke, Thesis, TU Braunschweig, FRG (1989)) in 100 ml water and cooled to -3° C. At this temperature 10 g isocyanatoethyl-methylacrylate (IEM, Dow Chemical) are added dropwise while stirring vigorously and during which the inner temperature is kept below 50° C. After completion of the isocyanate addition it is stirred for 12 hours and heated to room temperature. During the reaction time the emulsion which forms becomes a clear colourless solution. Subsequently the aqueous solution is extracted with ether in order to remove traces of undissolved isocyanate. After lyophilizing the solution the crude product is dissolved in methanol and recrystallized from acetone/ether (yield 35.3 g 95%); melting point 93° C. N-ethylmethacrylato-N'-1-deoxymaltitol urea (2), N-methylacrylato-N'-1-deoxycellobiitol urea (3) as well as N-ethylmethacrylato-N'-1-deoxylactitol urea (4) are produced in a corresponding manner from the corresponding 1-amino-1-deoxy sugars.

後処理

  1. customis kept below 50° C
  2. stirringis stirred for 12 hours
  3. temperatureheated to room temperature
  4. extractionSubsequently the aqueous solution is extracted with ether in order
  5. customto remove traces of undissolved isocyanate
  6. dissolutionis dissolved in methanol
  7. customrecrystallized from acetone/ether (yield 35.3 g 95%)

出典と根拠

ORDレコード
ord-e6ea2e944a6d435fa6c0273630c3035b
出典データセット
uspto-grants-1996_01
特許番号
US05480790

関連ノート

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