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Tetrabutylammonium Fluoride → 1,1-Dimethylethyl {[3'-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate

HRID 564481
ノート
印刷プレビュー

反応式

HRID 564481 の反応式
CC([Si](C)(C)[O:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 578132741,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate

生成物 1

HCID 578132931,1-Dimethylethyl {[3'-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate (1.5 g, 3.28 mmol) in THF (20 mL), the solution of nBu4NF (0.94 g, 3.61 mmol) in THF (10 mL) was added, and then the mixture was stirred at room temperature over night. After the solvent was removed under reduced pressure, the residue was diluted with EtOAc (30 mL). The organic layer was washed with water (10 mL×2), brine (10 mL×2), and dried over Na2SO4. The product 1,1-dimethylethyl {[3′-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate (0.9 g) was purified by flash column chromatography (PE:EA=3:1). (Yield: 80%). 1H NMR (400 MHz, CDCl3): δ 1.47 (s, 9 H), 3.86 (s, 3 H), 4.35 (d, J=7.6 Hz, 2 H), 4.76 (s, 2 H), 4.89 (s, 1 H), 6.83 (s, 1 H), 7.02 (s, 1 H), 7.09 (s, 1 H), 7.34-7.58 (m, 4H); 13C NMR (100 MHz, CDCl3): δ 28.4, 44.7, 55.4, 65.2, 79.6, 111.9, 118.7, 125.8, 126.1, 126.4, 129.0, 140.9, 141.2, 141.5, 142.8, 156.0, 160.3. HPLC: retention time: 11.558 min; purity: 98.7%; MS: m/z 343 (M+).

後処理

  1. customAfter the solvent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (30 mL)
  3. washThe organic layer was washed with water (10 mL×2), brine (10 mL×2)
  4. dry with materialdried over Na2SO4
  5. customThe product 1,1-dimethylethyl {[3′-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate (0.9 g) was purified by flash column chromatography (PE:EA=3:1)

出典と根拠

ORDレコード
ord-5905e7e506324275b32124d2013db2d4
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08067408B2

反応ノート

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