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Potassium Carbonate → {3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic Acid Methyl Ester

HRID 902672
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HRID 902672 반응식
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@@H:14](OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:15])[CH:6]=1.[C:28]1([C@H:34]([CH3:37])[CH2:35][NH2:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@H:14]([NH:36][CH2:35][C@H:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:37])[CH3:15])[CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1547950(2S)-2-Phenylpropan-1-amineHCID 86598128(S)-{3-[3-(Toluene-4-sulfonyloxy)-butoxy]-phenyl}-acetic acid methyl ester

생성물 1

HCID 69254631{3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic Acid Methyl Ester수율 66.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of {3-[(S)-3-(Toluene-4-sulfonyloxy)-butoxy]-phenyl}-acetic acid methyl ester (0.2 g, 0.51 mmol) and (S)-2-Phenyl-propylamine (0.19, 0.77 mmol) in acetonitrile (30 ml) was treated with solid potassium carbonate (0.149, 1.02 mmol). The reaction was heated to reflux and stirred for six days. Upon cooling to room temperature, the reaction was filtered through a pad of celite, washed with EtOAc, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatograph (EtOAc:Hexane/20:80) to give the title compound as an oil (0.12 g, 40%). MS m/e 356.6 (M+H)+.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationthe reaction was filtered through a pad of celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatograph (EtOAc:Hexane/20:80)

출처 및 근거

ORD 기록
ord-3deb0bc82f264f4fae3aa094ad99fc6e
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365085B2

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