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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester

HRID 580830
ノート
印刷プレビュー

反応式

HRID 580830 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:36]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:37]([C:40](O)=[O:41])[CH2:38][OH:39].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[CH2:12]([O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:22][C:38](=[O:39])[C@H:37]([CH2:40][OH:41])[NH:36][C:43]([O:45][C:46]([CH3:47])([CH3:49])[CH3:48])=[O:44])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 13233366L-Glutamic acid dibenzyl ester tosylate

生成物 1

HCID 67584326N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester収率 94.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of L-glutamic acid 1,5-dibenzyl ester p-toluenesulfonate (10.0 g), Boc-Ser (4.1 g) and TEA (2.0 g) in DMF (200 ml) are added with stirring WSC (5.0 g) and HOBt (4.0 g) under ice-cooling. The mixture is stirred at room temperature for 20 hours, and thereto is added ethyl acetate (200 ml). The mixture is washed successively with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The precipitated solid is collected by filtration, and washed with ether to give N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester (9.7 g) as colorless crystals.

後処理

  1. temperaturecooling
  2. washThe mixture is washed successively with 1N hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitated solid is collected by filtration
  6. washwashed with ether

出典と根拠

ORDレコード
ord-a409ba1f32764a15a36baead25c90546
出典データセット
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05919769

反応ノート

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