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Water → 2-Tert-butoxycarbonylamino-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

HRID 1988281
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HRID 1988281 반응식
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[C:16]([C:20]1[CH:21]=[C:22]([CH2:27][CH:28]([NH2:34])[C:29]2[S:30][CH:31]=[CH:32][N:33]=2)[CH:23]=[CH:24][C:25]=1[OH:26])([CH3:19])([CH3:18])[CH3:17].O>C1COCC1>[C:16]([C:20]1[CH:21]=[C:22]([CH2:27][CH:28]([NH:34][C:6](=[O:8])[CH:2]([NH:1][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]([CH3:4])[CH3:5])[C:29]2[S:30][CH:31]=[CH:32][N:33]=2)[CH:23]=[CH:24][C:25]=1[OH:26])([CH3:19])([CH3:17])[CH3:18]
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참가 물질

5

반응물 3

HCID 962WaterHCID 83693Boc-L-ValineHCID 178192062-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

생성물 1

HCID 876058412-Tert-butoxycarbonylamino-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide수율 106%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Boc-Val-OH (890 mg, 4.09 mmol), 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamine (1.03 g, 3.73 mmol) and CMPI (653 mg, 1.05 mmol) in THF (10 ml), TEA (1 ml) was added under cooling with ice and stirred at room temperature overnight. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium 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 (1.88 g, 99%).

후처리

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

출처 및 근거

ORD 기록
ord-21f82f36e5a84cf49f8a2bfadfbb73ff
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07553969B1

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