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Potassium Carbonate → Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate

HRID 1375723
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HRID 1375723 반응식
CS([O:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1)(=O)=O.[CH2:23]([O:25][C:26](=[O:39])[C@@H:27]([O:36][CH2:37][CH3:38])[CH2:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:19]([O:18][C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][O:5][C:32]2[CH:31]=[CH:30][C:29]([CH2:28][C@H:27]([O:36][CH2:37][CH3:38])[C:26]([O:25][CH2:23][CH3:24])=[O:39])=[CH:34][CH:33]=2)=[CH:10][CH:11]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 219936273-{4-[(Tert-butoxycarbonyl)amino]phenyl}propyl methanesulfonate

생성물 1

HCID 86613339Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate수율 75.5%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propyl methanesulfonate (360 mg, 1.093 mmol) and (S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (260 mg, 1.093 mmol) were mixed in acetonitrile (30 ml). Potassium carbonate (anhydrous, 226.6 mg 1.639 mmol) was added. The mixture was heated to reflux overnight and thereafter it was evaporated to dry. Ethyl acetate (20 ml) and water (5 ml) were added into the residue. The two phases were separated and the water phase was extracted with ethyl acetate (10 ml×2). The organic phases were combined and washed with 0.1 M sodium hydroxide aqueous solution, water and brine and dried with magnesium sulfate. The solvent was evaporated in vacuum and an oil mixture was left. Column chromatography of the oil mixture on silica gel using ethyl acetate/heptane (20:80) as eluant gave the desired product (389 mg), yield 75.5%.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customit was evaporated
  4. customto dry
  5. additionEthyl acetate (20 ml) and water (5 ml) were added into the residue
  6. customThe two phases were separated
  7. extractionthe water phase was extracted with ethyl acetate (10 ml×2)
  8. washwashed with 0.1 M sodium hydroxide aqueous solution, water and brine
  9. dry with materialdried with magnesium sulfate
  10. customThe solvent was evaporated in vacuum
  11. waitan oil mixture was left

출처 및 근거

ORD 기록
ord-6e3a5db504a44cc1b453b1905b3b7e00
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169810B2

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