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Diethyl Ether → 2-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid

HRID 1058932
ノート
印刷プレビュー

反応式

HRID 1058932 の反応式
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-:25].[Na+].[CH3:27][CH2:28]OCC.C[C:33](=[O:36])[CH2:34][CH3:35]>>[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:34]([CH3:35])([CH2:27][CH3:28])[C:33]([OH:36])=[O:25])=[CH:18][CH:19]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 6569Methyl Ethyl Ketone2 回HCID 14798Sodium HydroxideHCID 14103856benzyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

生成物 1

HCID 186694352-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid

反応条件

温度
30 °C

実験手順

A solution of 4-(2-(phenylmethyloxycarbonylamino)ethyl)phenol (5.74 g; 21.16 mmole) in 2-butanone (17 mL) and chloroform (6 g) was added dropwise to a mixture of sodium hydroxide (9.0 g; 225 mmole) and 2-butanone (67 mL) whilst keeping the reaction temperature below 30° C. The mixture was allowed to stir at 30° C. for 4 h. Ether (100 mL) was added and the resultant solid was collected by filtration and washed with ether (100 mL). The solid was dissolved in water (70 mL) and any residual ether removed by evaporation. 1N Hydrochloric acid was added to adjust the pH to 1, and the resulting oil was extracted with dichloromethane (3×50 mL). The combined extracts were dried (Na2SO4) and evporated to afford a yellow oil (3.82 g; 49%). 1H-NMR (CDCl3) δ 7.26 (s, 5H), 7.09 (d, 2H, J=7.9 Hz), 6.88 (d, 2H, J=8.4 Hz), 5.09 (s, 2H), 4.75 (br s, 1H), 3.42-3.44 (m, 2H), 2.75 (t, 2H, J=6.7 Hz), 1.92-2.00 (m, 2H), 1.47 (s, 3H), 1.04 (t, 3H, J=2.6 Hz). Mass spectrometry ES+, m/e (M+H)+=372.

後処理

  1. customthe reaction temperature below 30° C
  2. filtrationthe resultant solid was collected by filtration
  3. washwashed with ether (100 mL)
  4. dissolutionThe solid was dissolved in water (70 mL)
  5. customany residual ether removed by evaporation
  6. addition1N Hydrochloric acid was added
  7. extractionthe resulting oil was extracted with dichloromethane (3×50 mL)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customto afford a yellow oil (3.82 g; 49%)

出典と根拠

ORDレコード
ord-bf79c1dd1d3543c38d62ef3069e6df4b
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06518290B1

反応ノート

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