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

HRID 254370노트

반응식

HRID 254370 반응식
[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

참가 물질

6

반응물 2

HCID 21185506HCID 21185506, 화합물HCID 29404500[2-(4-Iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9795a5091ea94f40b4342a55f127d035
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875619B2

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