1-Benzoyl-2-isopropylhydrazine → Benzoic acid N'-[3-(5-fluoro-2-propoxy-phenyl)-propionyl]-N'-isopropyl-hydrazide

HRID 1724159

반응식

HRID 1724159 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:7]=1.[CH:17]([NH:20][NH:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:19])[CH3:18].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH2:8][CH2:9][C:10]([N:20]([CH:17]([CH3:19])[CH3:18])[NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:12])[CH:7]=1

참가 물질

6

반응물 4

HCID 188691-Benzoyl-2-isopropylhydrazineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 687991413-(5-Fluoro-2-propoxy-phenyl)-propionic acid

생성물 1

HCID 57560120Benzoic acid N'-[3-(5-fluoro-2-propoxy-phenyl)-propionyl]-N'-isopropyl-hydrazide수율 36.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-(5-fluoro-2-propoxy-phenyl)-propionic acid (160 mg, 0.71 mmoles) and benzoic acid N′-isopropyl-hydrazide (106 mg, 0.60 mmoles) in DMF (3 mL) was treated with diisopropylethylamine (0.26 mL, 1.49 mmoles), and PyBroP (416 mg, 0.89 mmoles) at room temperature for 16 h. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient to afford the product as a solid (84 mg, 30%). LC-MS m/e 387.26 (M+H+)

후처리

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-bcc4b4ebbdbe46da8d0f508983d5f610
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485752B2

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