Methanol → 1-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid

HRID 2068525노트

반응식

HRID 2068525 반응식
[CH2:1]([O:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]2)=[O:9])=[CH:6][CH:5]=1)[CH3:2].O1CCCC1.CO.[OH-].[Li+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)=[O:9])=[CH:19][CH:20]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58304093Ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate

생성물 1

HCID 583041121-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid수율 99.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

Add ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate (478 g, 1.72 mol) to tetrahydrofuran (2 L) and methanol (1 L). Dissolve lithium hydroxide (LiOH) (144.7 g, 3.45 mol) in water (1 L) and add it to the mixture. Stir the reaction mixture while heating to 55° C. Cool the reaction to ambient temperature and concentrate under reduced pressure. After removing 2.5 L of solvent, dilute the mixture with water (2 L) and immerse it in an ice water bath. Adjust to pH 2 with aqueous 5N hydrochloric acid (750 mL). Filter the precipitate, wash the cake with water (2×2 L), and dry to give the title compound (425 g, 99%) as a white powder: MS (m/z): 250 (M+1).

후처리

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. concentrationconcentrate under reduced pressure
  4. customAfter removing 2.5 L of solvent
  5. additiondilute the mixture with water (2 L)
  6. filtrationFilter the precipitate
  7. washwash the cake with water (2×2 L)
  8. customdry

출처 및 근거

ORD 기록
ord-96efa7d14b8349d7a7def82f7dd0264d
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299061B2

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