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Propylamine → (3R)-6-cyclohexyl-3-{3-[(propylamino)carbonyl]-1,2,4-oxadiazol-5-yl}hexanoic acid

HRID 1279818
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HRID 1279818 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([C:20]([O:22]CC)=O)[N:16]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:25]([NH2:28])[CH2:26][CH3:27]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([C:20]([NH:28][CH2:25][CH2:26][CH3:27])=[O:22])[N:16]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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참가 물질

5

반응물 2

HCID 7852PropylamineHCID 59909750(3R)-6-cyclohexyl-3-[3-(ethoxycarbonyl)-1,2,4-oxadiazol-5-yl]hexanoic acid

생성물 1

HCID 59909837(3R)-6-cyclohexyl-3-{3-[(propylamino)carbonyl]-1,2,4-oxadiazol-5-yl}hexanoic acid수율 69.8%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
125 °C

실험 절차

A solution of (3R)-6-cyclohexyl-3-[3-(ethoxycarbonyl)-1,2,4-oxadiazol-5-yl]hexanoic acid (Preparation 4) (107 mg, 0.31 mmol) in toluene (2 ml) was treated with n-propylamine (250 μl, 3.10 mmol) and the mixture was heated at 125° C. in a sealed vessel for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed sequentially with aqueous citric acid solution (5% w/v), water and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:ethyl acetate (80:20) gradually changing to dichloromethane:ethyl acetate (60:40) then to dichloromethane:methanol (90:10) to afford the title compound as an oil (76 mg).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed sequentially with aqueous citric acid solution (5% w/v), water and brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:ethyl acetate (80:20)

출처 및 근거

ORD 기록
ord-80f5249a7fe045fea479c9fd71b29b5a
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06448278B2

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