2-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide → 3-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

HRID 1988277노트

반응식

HRID 1988277 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:34])[CH:21]([N:25](C(OC(C)(C)C)=O)[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:34])[CH:21]([NH:25][CH3:26])[CH:22]([CH3:23])[CH3:24])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:2])([CH3:4])[CH3:3]

참가 물질

4

반응물 1

HCID 867609042-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

생성물 1

HCID 867609033-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 2-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide (8.03 g, 16.42 mmol) in methylene chloride (80 ml), TFA (40 ml) was added and stirred at room temperature for 30 min. The reaction mixture was evaporated to remove the solvent under reduced pressure; the thus obtained residue was mixed with methylene chloride, washed with a 2N aqueous sodium hydroxide solution and 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: acetone:hexane=1:2), giving two diastereoisomers A and B of the titled compound, A (2.37 g, 37%) being eluted first and then B (2.17 g, 34%). (A)

후처리

  1. customThe reaction mixture was evaporated
  2. customto remove the solvent under reduced pressure
  3. additionthe thus obtained residue was mixed with methylene chloride
  4. washwashed with a 2N aqueous sodium hydroxide solution and 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-2dd4becd7e5a46e2b01ceeec288c4656
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553969B1

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