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

HRID 392926

반응식

HRID 392926 반응식
[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]

참가 물질

3

반응물 1

HCID 892442-(4-Nitrophenyl)propionic acid

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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). Reslurried 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), 4.18-4.20 (m, 1H), 7.27-7.53 (aromatic, 7H), 8.09-8.12 (aromatic, 2H);

후처리

  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

출처 및 근거

ORD 기록
ord-a1970d239e7e47bda6108ede950d0f7d
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803484B2

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