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Water → ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

HRID 1354547
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HRID 1354547 반응식
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:5](=[O:17])[CH2:4]1)[CH3:2].Cl.[CH2:19](O)[CH3:20].[OH2:22]>C(OCC)(=O)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([O:17][CH2:19][CH3:20])=[O:22])=[CH:8][CH:9]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 21887872Ethanol hydrochloride

생성물 1

HCID 57888577ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

To 200 mg (0.822 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6, 2.0 g (16.45 mmol) of 30 wt % hydrogen chloride/ethanol solution was added dropwise for 5 minutes. On completion of the addition, the resulting solution was heated to 40° C. and stirred for 14 hours. Water (5 mL) was added to the solution and extraction with ethyl acetate was carried out. The extracted organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate as a yellow oil (193.8 mg, crude yield: 82%). 1H-NMR (CDCl3, 400 MHz/ppm): 6 0.98 (3H, t), 1.23 (3H, t), 1.55-1.71 (2H, m), 2.53 (2H, m), 3.75-3.82 (1H, m), 4.11 (2H, q), 6.61 (2H, d), 7.38 (2H, d)

후처리

  1. additionOn completion of the addition
  2. washThe extracted organic layer was washed with saturated brine
  3. dry with materialthe product was dried with anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-73fe19ce2e774848ad86095eb599e904
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07223859B2

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