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Chlorotrimethylsilane → 3-(4-Boronophenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

HRID 1424315
ノート
印刷プレビュー

反応式

HRID 1424315 の反応式
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([B:13]([OH:15])[OH:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].CCN(C(C)C)C(C)C.C[Si](Cl)(C)C.[CH3:30][C:31]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[C:32]=1[C:33](Cl)=[O:34]>C(Cl)Cl>[B:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:2]([NH:1][C:33](=[O:34])[C:32]2[C:36]([CH3:41])=[CH:37][C:38]([CH3:40])=[CH:39][C:31]=2[CH3:30])[C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)([OH:15])[OH:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 53503p-BoronophenylalanineHCID 81531DiisopropylethylamineHCID 970382,4,6-Trimethylbenzoyl chloride

生成物 1

HCID 576609483-(4-Boronophenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒
3 回

実験手順

1.5 g (7.18 mmol) of 2-amino-3-(4-boronophenyl)propionic acid were suspended in 50 ml DCM and 7.4 ml (43.1 mmol) DIPEA and refluxed for 20 min together with 4.5 ml (35 mmol) TMSCl. The solution was cooled in an ice bath and a solution of 1.44 g (7.9 mmol) 2,4,6-trimethylbenzoyl chloride in 5 ml DCM were added dropwise. The reaction mixture was stirred 2 h at room temperature, diluted with 100 ml DCM and washed with 2 N aqueous HCl. During this washing some product precipitated which was collected. The organic phase was extracted with 2 N NaOH twice. Upon acidifying of the combined basic phases the product precipitated, which was collected and dried together with the first precipitate. The crude product was used without further purification.

後処理

  1. temperatureThe solution was cooled in an ice bath
  2. washwashed with 2 N aqueous HCl
  3. customDuring this washing some product precipitated which
  4. customwas collected
  5. extractionThe organic phase was extracted with 2 N NaOH twice
  6. customprecipitated
  7. customwhich was collected
  8. customdried together with the first precipitate
  9. customThe crude product was used without further purification

出典と根拠

ORDレコード
ord-0c7bef94f99d4f2da8782cb9b47e5567
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927534B2

反応ノート

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