Triphenylphosphine → 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide

HRID 1454827노트

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HRID 1454827 반응식
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]([F:45])([F:44])[C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH3:13][C:11]([CH3:12])([CH3:14])[C:10]([NH:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][O:1][C:40]2[CH:41]=[CH:42][C:37]([C:36]([F:45])([F:44])[F:35])=[CH:38][CH:39]=2)[N:8]=1)=[O:15]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21782926N-[6-(Hydroxymethyl)pyridin-2-yl]-2,2-dimethylpropanamide

생성물 1

HCID 688432242,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide수율 92.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

N-(6-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (0.625 g), triphenylphophine (0.786 g) and 4-trifluoromethyl-phenol (0.486 g) in toluene was treated at RT under an argon atmosphere with diisopropyl azodicarboxylate (0.67 g). The mixture was stirred for 2 h, partitioned between ice water and AcOEt, the layers were separated, the aqueous layer twice extracted with AcOEt. The combined organic layers were washed with water and saturated aqueous NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100 to 85%) to give 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide (0.98 g) as a yellow oil. MS (ESI): 353.2 (MH+).

후처리

  1. custompartitioned between ice water and AcOEt
  2. customthe layers were separated
  3. extractionthe aqueous layer twice extracted with AcOEt
  4. washThe combined organic layers were washed with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography (heptane/AcOEt 100 to 85%)

출처 및 근거

ORD 기록
ord-95b6212040154c8ea5f1448012f0e1a4
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482341B2

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