Triethylamine → HCID 24805217、化合物

HRID 1927798ノート

反応式

HRID 1927798 の反応式
C(O[C:6]([N:8]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:22])=[O:15])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])(C)(C)C.C(N(CC)CC)C.C(Cl)(=O)[C:31]1[C:32]([O:37][CH3:38])=[CH:33][CH:34]=[CH:35][CH:36]=1>FC(F)(F)C(O)=O>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:6]([N:8]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:22])=[O:15])[CH2:9][CH:10]([CH3:11])[CH3:12])=[O:7]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 68711938HCID 68711938、化合物

生成物 1

HCID 24805217HCID 24805217、化合物収率 66%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

(2S)-1-(2-(N-tert-Butyloxycarbonyl-N-(2-methylpropyl)amino)acetyl)pyrrolidine-2-carbonitrile (25 mg, 0.081 mmol) was treated with trifluoroacetic acid (50 ml). After 1 h at room temperature the solvent was removed in vacuo and the residue dissolved in CH2Cl2 (100 ml). The solution was cooled to 0° C., triethylamine (30 mg, 0.3 mmol) was added followed by 2-anisoyl chloride (15 mg, 0.088 mmol). After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue dissolved in ethyl acetate (200 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 2% methanol, 98% chloroform) to give a colourless oil identified as the title compound (18 mg, 0.052 mmol, 66%).

後処理

  1. customAfter 1 h at room temperature the solvent was removed in vacuo
  2. dissolutionthe residue dissolved in CH2Cl2 (100 ml)
  3. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate (200 ml)
  5. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (eluant: 2% methanol, 98% chloroform)
  9. customto give a colourless oil

出典と根拠

ORDレコード
ord-1d9f13dff1094bde955b4b8d65eaf446
出典データセット
uspto-grants-2012_05
特許番号
US08183280B2

反応ノート

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