Hydrogen Peroxide → (5-{2-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid

HRID 554618노트

반응식

HRID 554618 반응식
[CH2:1]([N:3]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C:20]1[C:21]([O:32][CH3:33])=[N:22]C=C(C#C[Si](C)(C)C)[CH:25]=1)C(C1CC1)=O)[CH3:2].[O:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.B.[OH:40]O.[OH-].[Na+].[CH2:44]1[CH2:48][O:47][CH2:46][CH2:45]1>CO>[CH:37]1([C:38]([N:3]([CH2:9][C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=2[C:20]2[CH:25]=[C:44]([CH2:45][C:46]([OH:40])=[O:47])[CH:48]=[N:22][C:21]=2[O:32][CH3:33])[CH2:1][CH3:2])=[O:34])[CH2:35][CH2:36]1

참가 물질

7

반응물 5

HCID 784Hydrogen Peroxide2회HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 67212431Cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide

생성물 1

HCID 45138482(5-{2-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide (0.205 g, 0.42 mmol) in THF (2 mL) at 0° C. was added borane tetrahydrofuran complex (1M in THF; 0.48 mL, 0.48 mmol), and the reaction was stirred for 2 hours. Once no starting material was seen by analytical LCMS, MeOH (0.22 mL), hydrogen peroxide (0.04 mL, 0.43 mmol), and 3M aqueous sodium hydroxide (0.22 ml) was added, and the reaction was stirred for 1 hour. Additional hydrogen peroxide (0.1 mL) was added, and the reaction was stirred for another hour. The mixture was then acidified and extracted with EtOAc, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by preparative HPLC to give Compound 10.

후처리

  1. additionwas added
  2. stirringthe reaction was stirred for 1 hour
  3. stirringthe reaction was stirred for another hour
  4. extractionextracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-1f32a24ebee64fc39a0f621e98e9a093
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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