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Bromotrimethylsilane → {2-[4-(6-Ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enylamino]-ethyl}-phosphonic acid

HRID 2282051
ノート
印刷プレビュー

反応式

HRID 2282051 の反応式
C([O:3][P:4]([CH2:9][CH2:10][NH:11][CH2:12][C:13]([CH3:36])=[CH:14][CH2:15][C:16]1[C:17]([O:29]CC[Si](C)(C)C)=[C:18]2[C:22](=[C:23]([CH3:27])[C:24]=1[CH2:25][CH3:26])[CH2:21][O:20][C:19]2=[O:28])(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>CN(C=O)C.C(Cl)Cl>[CH2:25]([C:24]1[C:23]([CH3:27])=[C:22]2[C:18]([C:19](=[O:28])[O:20][CH2:21]2)=[C:17]([OH:29])[C:16]=1[CH2:15][CH:14]=[C:13]([CH3:36])[CH2:12][NH:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[CH3:26]
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 2

HCID 76113BromotrimethylsilaneHCID 72563615(2-{4-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enylamino}-ethyl)-phosphonic acid diethyl ester

生成物 1

HCID 67011616{2-[4-(6-Ethyl-4-hydroxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enylamino]-ethyl}-phosphonic acid収率 72.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒

実験手順

(2-{4-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enylamino}-ethyl)-phosphonic acid diethyl ester (27.7 mg, 0.051 mmol) was dissolved in DMF (0.5 mL) and DCM (0.5 mL). Trimethylsilyl bromide (78.3 mg, 0.512 mmol) was added and the reaction was stirred at room temperature. After 20 hrs the reaction was quenched with MeOH (0.3 mL). The solvents were evaporated in vacuo and the crude material was purified by RP-HPLC (eluent: water/MeCN). The product-containing fractions were combined and lyophilized to yield 14.2 mg (57%) of the free phosphonic acid [MS: 484 M++1].

後処理

  1. customAfter 20 hrs the reaction was quenched with MeOH (0.3 mL)
  2. customThe solvents were evaporated in vacuo
  3. customthe crude material was purified by RP-HPLC (eluent: water/MeCN)

出典と根拠

ORDレコード
ord-fb54ab97141c4c409bc977f98f1be37f
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139604B2

反応ノート

読み込み中…

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