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1-Phenethylamine → 1-Phenethylamine, (-)-

HRID 443102
ノート
印刷プレビュー

反応式

HRID 443102 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]([F:25])([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[N+:22]([O-:24])=[O:23])[C:9]([OH:11])=[O:10])[CH:7]=1.[CH3:28][CH:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)(C)C>[CH3:28][C@H:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C@@:8]([F:25])([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][C:13]=2[N+:22]([O-:24])=[O:23])[C:9]([OH:11])=[O:10])[CH:7]=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

5

反応物 2

HCID 74081-PhenethylamineHCID 154087405-Chloro-alpha-fluoro-2-methoxy-alpha-[2-nitro-4-(trifluoromethyl)-phenyl]benzeneacetic acid

生成物 2

HCID 758181-Phenethylamine, (-)-収率 41%HCID 15408741(alphaS)-alpha-Fluoro-alpha-(2-methoxy-5-chlorophenyl)-2-nitro-4-(trifluoromethyl)benzeneacetic acid

試薬・触媒・溶媒 1

HCID 3776
Isopropanol
溶媒

反応条件

温度
50 °C

実験手順

A 5-L three-necked round-bottomed flask, equipped with a mechanical stirrer and thermocouple, was charged with the racemic acid of Example 4 (392.87 g, 0.964 mol) and dissolved in isopropanol (2.0 L) to afford a light yellow solution. While stirring vigorously the reaction mixture was heated to 50° C. and then (S)-(α-methylbenzylamine was added over five minutes, causing the reaction tp turn slightly green in color. Heating was discontinued and a seed crystal was preferably added. Crystallization was observed within 15 minutes. The reaction mixture was cooled to room temperature over 2 hours while stirring and then the crystals were collected by filtration and washed with isopropanol (500 mL). After drying under vacuum, 208 g of the title compound as a 1:1 salt with (S)-α-methylbenzylamine (41% yield corrected for about 9% of 2-propanol as determined by 1H NMR; about 99.9% by HPLC) was obtained as a fluffy white solid. The product was found to be 99.3% enantiomerically pure as determined by capillary electrophoresis.

後処理

  1. customA 5-L three-necked round-bottomed flask, equipped with a mechanical stirrer
  2. customto afford a light yellow solution
  3. temperatureHeating
  4. additiona seed crystal was preferably added
  5. customCrystallization
  6. temperatureThe reaction mixture was cooled to room temperature over 2 hours
  7. stirringwhile stirring
  8. filtrationthe crystals were collected by filtration
  9. washwashed with isopropanol (500 mL)

出典と根拠

ORDレコード
ord-75c383ddb8c04c8f935bacc2474e9be7
出典データセット
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05892106

反応ノート

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