Water → 2-((2-butoxycarbonylamino-3-(4-fluorophenyl)propionyl)-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide

HRID 1988248노트

반응식

HRID 1988248 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:23][C:24](=[O:31])[CH:25]([NH:29][CH3:30])[CH:26]([CH3:28])[CH3:27])[C:14](=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[NH:32]([C:45]([O:47][C:48]([CH3:51])(C)C)=[O:46])[C@H:33]([C:42]([OH:44])=O)[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1.O.[CH2:53]1COC[CH2:54]1>>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:23][C:24](=[O:31])[CH:25]([N:29]([C:42](=[O:44])[CH:33]([NH:32][C:45]([O:47][CH2:48][CH2:51][CH2:53][CH3:54])=[O:46])[CH2:34][C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[CH3:30])[CH:26]([CH3:27])[CH3:28])[C:14](=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:3])([CH3:2])[CH3:4]

참가 물질

5

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanineHCID 867608933-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide

생성물 1

HCID 867608962-((2-butoxycarbonylamino-3-(4-fluorophenyl)propionyl)-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide수율 85%

실험 절차

To a solution of 3-methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide (1.25 g, 2.93 mmol), Boc-Phe(4-F)-OH (1.08 g, 3.81 mmol) and CMPI (973 mg, 3.81 mmol) in THF 19 ml, TEA (0.94 ml, 6.74 mmol) was added under cooling with ice and stirred for 4 hours under cooling with ice. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1), giving the titled compound (1.72 g, 85%).

후처리

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-16f5d052f93549be985e73e77c7e102c
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553969B1

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