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3,5-Dinitrobenzoyl chloride → ethyl (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

HRID 2386108
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HRID 2386108 반응식
Cl.[NH2:2][C@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=1)[C:29](Cl)=[O:30])([O-:25])=[O:24]>O1CCCC1>[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=1)[C:29]([NH:2][C@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:30])([O-:25])=[O:24]
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참가 물질

5

반응물 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 22831526(S)-Ethyl 3-amino-3-phenylpropanoate hydrochloride

생성물 1

HCID 44255974ethyl (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
5 °C

실험 절차

11.49 g of ethyl (S)-3-amino-3-phenylpropionate hydrochloride were suspended in 100 ml of tetrahydrofuran and cooled to 0-10° C. in an icebath. After adding 14 ml of triethylamine, a solution of 11.52 g of 3,5-dinitrobenzoyl chloride in 40 ml of tetrahydrofuran was added with stirring and cooling over a period of 30 min. The cooling bath was removed, and the reaction mixture stirred for a further 120 min, in the course of which it warmed to room temperature. The reaction mixture was filtered, and the filtrate concentrated to dryness (product fraction 1). The filtercake—consisting of triethylamine hydrochloride and further product—was taken up in 100 ml of ethyl acetate and digested at 35° C. for 20 min. The suspension was filtered, and the filtercake discarded. The filtrate was concentrated to dryness under reduced pressure at 40° C. (product fraction 2). The product fractions were combined. Yield: 16.4 g; HPLC purity>97 area %. For further purification, the crude product was digested in 400 ml of water at room temperature for 2 h and then filtered. The moist yield was 15.4 g; HPLC purity 99.8 area %. The product was reacted further without further purification.

후처리

  1. temperaturecooling over a period of 30 min
  2. customThe cooling bath was removed
  3. stirringthe reaction mixture stirred for a further 120 min, in the course of which it
  4. temperaturewarmed to room temperature
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate concentrated to dryness (product fraction 1)
  7. filtrationThe suspension was filtered
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure at 40° C. (product fraction 2)
  9. customFor further purification
  10. waitthe crude product was digested in 400 ml of water at room temperature for 2 h
  11. filtrationfiltered
  12. customThe product was reacted further without further purification

출처 및 근거

ORD 기록
ord-8907f71cb72c4a90b8135ba30df662a3
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08268631B2

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