HCID 21185506、化合物 → {4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester

HRID 254370ノート

反応式

HRID 254370 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][C:10](=[O:19])[NH:11][C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29](=[O:35])[NH:30][CH2:31][CH2:32][C:33]#[CH:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(N(CC)CC)C>[CH2:21]([O:28][C:29](=[O:35])[NH:30][CH2:31][CH2:32][C:33]#[C:34][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:10](=[O:19])[CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:20])=[CH:13][CH:14]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 2

HCID 21185506HCID 21185506、化合物HCID 29404500[2-(4-Iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

生成物 1

HCID 58664814{4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

To a solution of [2-(4-iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester 310 (1.5 g, 3.84 mmol), and triethylamine (40 mL) was added trans-dichlorobis-(triphenylphosphine)palladium (II) (Ph3P, PdCl2, 0.27 g, 0.38 mmol). The reaction mixture was stirred for 20 minutes when it became a clear solution. But-3-ynyl-carbamic acid benzyl ester (0.94 g, 4.6 mmol) and copper iodide (0.14 g, 0.768 mmol) were then added and the reaction was further stirred at room temperature for 18 hours. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane (100 mL) and washed with water (3×150 mL). The organic layer was dried over sodium sulfate and then concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 1:1, v/v hexanes/ethyl acetate) to provide 320 (1.91 g, still a mixture, but used as it was without further purification). 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 2.60 (m, 4H), 3.47 (m, 4H), 5.12 (s, 2H), 7.37 (m, 7H), 7.49 (d, 2H).

後処理

  1. stirringthe reaction was further stirred at room temperature for 18 hours
  2. customThe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  4. washwashed with water (3×150 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, 1:1, v/v hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-9795a5091ea94f40b4342a55f127d035
出典データセット
uspto-grants-2011_01
特許番号
US07875619B2

反応ノート

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