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Potassium Iodide → HCID 11014455、化合物

HRID 2254390
ノート
印刷プレビュー

反応式

HRID 2254390 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@H:8]([NH:12][C:13](=[O:22])[C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:25]([CH2:24][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@H:8]([NH:12][C:13](=[O:22])[C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1)([O:27][CH2:28][CH3:29])=[O:26]
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 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10108652HCID 10108652、化合物

生成物 1

HCID 11014455HCID 11014455、化合物収率 57%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 15.8 g of N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-mandelamide, obtained according to Example 3(b), 7.1 ml of ethyl bromoacetate, 22 g of anhydrous potassium carbonate and 1 g of potassium iodide in 600 ml of anhydrous acetone, is heated with reflux and with stirring for 5 hours and a half. The reaction mixture is filtered, evaporated to dryness and the oil which separates is left to crystallize. The solid so obtained is purified by flashchromatography (elution with a 1/1 mixture of ethyl acetate/cyclohexane). The solid on the column is taken up and treated with 20 ml of ethyl ether, filtered and crystallized from ethyl acetate to give 11.5 g of N-[(2S)-7-carbethoxymethoxy-1,2,3,4-tetrahydronaphth-2-yl]-(R)-mandelamide, SR 58638; m.p. 115°-117° C.; [alpha]=-98.3° (methanol, c=1%). Yield: 57%.

後処理

  1. customobtained
  2. temperatureis heated
  3. temperaturewith reflux
  4. filtrationThe reaction mixture is filtered
  5. customevaporated to dryness
  6. waitthe oil which separates is left
  7. customto crystallize
  8. customThe solid so obtained
  9. customis purified by flashchromatography (
  10. washelution
  11. additionwith a 1/1 mixture of ethyl acetate/cyclohexane)
  12. additiontreated with 20 ml of ethyl ether
  13. filtrationfiltered
  14. customcrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-f4bbcfb451e24ac8a6fd9aa929a2a5bb
出典データセット
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05235103

反応ノート

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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