ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

tert-Butyl bromoacetate → 1-[(tert-Butoxycarbonyl)methyl]-Nalpha-benzyloxycarbonyl-D-tryptophan

HRID 1108206
ノート
印刷プレビュー

反応式

HRID 1108206 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:18][C:19]([NH:21][C@@H:22]([C:33]([OH:35])=[O:34])[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Br[CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>O1CCCC1>[C:41]([O:40][C:38]([CH2:37][N:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([CH2:23][C@H:22]([C:33]([OH:35])=[O:34])[NH:21][C:19]([O:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:20])=[CH:25]1)=[O:39])([CH3:44])([CH3:43])[CH3:42]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 79177tert-Butyl bromoacetateHCID 700663N-(Benzyloxycarbonyl)-D-tryptophanHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 538032101-[(tert-Butoxycarbonyl)methyl]-Nalpha-benzyloxycarbonyl-D-tryptophan収率 101.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

600 ml of a solution of NaHMDS (sodium salt of 1,1,1,3,3,3-hexamethyldisilazane) (1M) in tetrahydrofuran are added dropwise, at -78° C. under an inert atmosphere, to a solution of 100 g of Nα-benzyloxycarbonyl-D-tryptophan in a liter of anhydrous tetrahydrofuran. After one hour, the temperature is brought to 0° C. and a solution of 64 g of tert-butyl bromoacetate in 50 ml of anhydrous tetrahydrofuran is added dropwise. The reaction mixture is then brought to ambient temperature and the solvent is subsequently evaporated off in vacuo. The residue is diluted with dichloromethane and the solution is acidified by adding an aqueous 4N hydrochloric acid solution. After extraction with dichloromethane, the organic phases are dried over sodium sulphate and then concentrated in vacuo. 136 g of the expected product are obtained.

後処理

  1. customis brought to 0° C.
  2. customis then brought to ambient temperature
  3. customthe solvent is subsequently evaporated off in vacuo
  4. additionThe residue is diluted with dichloromethane
  5. additionby adding an aqueous 4N hydrochloric acid solution
  6. extractionAfter extraction with dichloromethane
  7. dry with materialthe organic phases are dried over sodium sulphate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-858fd614e1bd497186f9d18efd6ddb17
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06066633

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート