2-(4-Nitrophenyl)propionic acid → (R)-2-(4-Nitrophenyl)propanoic acid

HRID 2085444ノート

反応式

HRID 2085444 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

3

反応物 1

HCID 892442-(4-Nitrophenyl)propionic acid

生成物 1

HCID 1485472(R)-2-(4-Nitrophenyl)propanoic acid

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

A 2 liter three necked flask equipped with a mechanical stirrer is charged with racemic 2-(4-nitrophenyl)propionic acid (40.55 grams, 0.208 mol) and ethyl acetate (1600.0 mL). To this solution at 30° C. was then added S(−)α-methylbenzylamine (13.49 mL, 0.104 mol) all at once. Reaction exothermed to 38° C. with massive formation of a white precipitate in less than 15.0 minutes. The reaction mixture was then heated at ethyl acetate reflux for 10.0 minutes and allowed to equilibrate to room temperature with stirring overnight. The precipitate was then filtered to give a semi-dried white product, (2R)-2-(4-nitrophenyl)propanoic acid, S(−)α-methylbenzylamine (wet cake=25.43 grams). Reslured the wet cake in ethyl acetate (1600.0 mL) at reflux for 10.0 minutes, stirred to room temperature overnight, and filtered the white precipitate, (2R)-2-(4-nitrophenyl)propanoic acid, S(−)α-methylbenzylamine, (wet cake=21.02 grams, ee=91.4%). Repeated the later again and dried the precipitate at 40° C. in a vacuum oven for 24.0 hours, (2R)-2-(4-nitrophenyl)propanoic acid, S(−)-α-methylbenzylamine, (18.02 g, 55%, ee=95%); 1H nmr (DMSO, 300 MHz) δ 1.31-1.32 (d, 3H), 1.37-1.38 (d, 3H), 3.56-3.60 (m, 1H), 4.184-20 (m, 1H), 7.27-7.53 (aromatic, 7H), 8.09-8.12 (aromatic, 2H); 13C nmr (DMSO, 300 MHz)) δ 19.91, 22.93, 48.45, 50.55, 123.71, 124.15, 127.15, 128.27, 129.06, 129.41, 129.76, 146.31, 153.36, 176.24.

後処理

  1. customat 30° C.
  2. customReaction
  3. waitexothermed to 38° C. with massive formation of a white precipitate in less than 15.0 minutes
  4. temperaturereflux for 10.0 minutes
  5. customto equilibrate to room temperature
  6. filtrationThe precipitate was then filtered

出典と根拠

ORDレコード
ord-7c9fd4c70f2a4d5eab563cd6841d8403
出典データセット
uspto-grants-2004_04
特許番号
US06720357B2

反応ノート

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