Chlorotrimethylsilane → L-Aspartic acid, N-(trimethylsilyl)-, bis(phenylmethyl) ester

HRID 649258ノート

反応式

HRID 649258 の反応式
[NH2:1][C@H:2]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH3:24][Si:25]([CH3:28])([CH3:27])Cl.C(N(CC)CC)C>C(OCC)C>[CH3:24][Si:25]([CH3:28])([CH3:27])[NH:1][C@H:2]([C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 2808532(S)-Dibenzyl 2-aminosuccinate

生成物 1

HCID 11373549L-Aspartic acid, N-(trimethylsilyl)-, bis(phenylmethyl) ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

The dibenzyl (S)-aspartate in anhydrous diethyl ether (200 ml) is cooled in an ice-bath under a nitrogen atmosphere. Trimethylchlorosilane (12.7 ml, 0.1 mole) is added to the stirred solution to give a white precipitate. Triethylamine (14.0 ml, 0.1 mole) is then added to the mixture. The cooling bath is removed and the mixture is stirred at room temperature (22°-25° C.) for 2 hrs. The mixture is then filtered directly into a 3-neck, 1.0 liter, round bottom flask fitted with a sintered glass funnel, magnetic sitrrer, and a vacuum-nitrogen inlet. This operation is carried out under a blanket of nitrogen, care being taken to exclude atmospheric moisture. The sintered glass funnel is replaced by a stopper and the ether is evaporated under vacuum with stirring to provide dibenzyl (S)-N-trimethylsilyl-aspartate (35.5 g, 0.092 mole) as a slightly hazy oil.

後処理

  1. customto give a white precipitate
  2. customThe cooling bath is removed
  3. filtrationThe mixture is then filtered directly into a 3-neck, 1.0 liter, round bottom flask
  4. customfitted with a sintered glass funnel
  5. customthe ether is evaporated under vacuum
  6. stirringwith stirring

出典と根拠

ORDレコード
ord-a7c0b778827a43a6b7e99ffaaa537829
出典データセット
uspto-grants-1988_04
特許番号
US04739048

反応ノート

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