Tetrabutylammonium Fluoride → N-(cyanomethyl)-4-methyl-2-{[4'-(1-piperazinyl)[1,1'-biphenyl]-3-yl]oxy}pentanamide

HRID 1744065ノート

反応式

HRID 1744065 の反応式
[C:1]([CH2:3][NH:4][C:5]([CH:7]([O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][N:28](C(O[Si](C(C)C)(C(C)C)C(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)C.C(OCC)(=O)C.O.C(=O)(O)[O-].[Na+]>[C:1]([CH2:3][NH:4][C:5](=[O:6])[CH:7]([O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]3)=[CH:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:2]

参加物

8

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 10282346Triisopropylsilyl 4-[3'-(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

生成物 1

HCID 10272735N-(cyanomethyl)-4-methyl-2-{[4'-(1-piperazinyl)[1,1'-biphenyl]-3-yl]oxy}pentanamide

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Triisopropylsilyl 4-[3′-(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)[1,1′-biphenyl]-4-yl]-1-piperazinecarboxylate (365 mg, 0.6 mmoles) in 8 mL of tetrahydrofuran was treated with tetrabutylammonium fluoride (0.75 mL, 1 M in THF, 0.75 mmoles) at 0° C. until the disappearance of the starting material was observed by TLC. The reaction was diluted with diethyl ether, ethyl acetate, water and sat. aq. sodium bicarbonate. The phases were separated, the organic phase washed with brine and dried over sodium sulfate. After concentration under reduced pressure, the residue was purified by flash chromatography (1% sat. aqueous ammonium hydroxide, 9% methanol, 90% dichloromethane) to afford N-(cyanomethyl)-4-methyl-2-{[4′-(1-piperazinyl)[1,1′-biphenyl]-3-yl]oxy}pentanamide. MS (−ESI): 405.3 [M−1]−.

後処理

  1. customThe phases were separated
  2. washthe organic phase washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was purified by flash chromatography (1% sat. aqueous ammonium hydroxide, 9% methanol, 90% dichloromethane)

出典と根拠

ORDレコード
ord-2827916379644f8db9cb0d09958ef59a
出典データセット
uspto-grants-2006_03
特許番号
US07012075B2

反応ノート

読み込み中…