참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | p-Ethynyltoluene | HCID 13018 | — |
| 반응물 | (R)-2-(5-Bromo-thiophene-2-sulfonylamino)-3-(1H-indol-3-yl)-propionic acid | HCID 11396269 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | S-3304 | HCID 10718956 | 55.4% |
반응 단계
In a round bottom flask was added crude (R)-2-(5-Bromo-thiophene-2-sulfonylamino)-3-(1H-indol-3-yl)-propionic acid (3) (60 mg, 0.14 mmol), p-tolyl acetylene 4 (480 mg, 0.41 mmol), PdCl2P(PPh3)2 (10 mg, 0.015 mmol), copper(I)iodide (2 mg, 0.01 mmol) and triethylamine (0.025 g, 0.25 mmol) and then dissolved in dry DMF (2 mL) under an atmosphere of nitrogen. The reaction mixture was then heated at 50° C. under a nitrogen atmosphere for 2 hours. The reaction mixture was then cooled to room temperature and diluted with ethyl acetate and washed with a solution composed of NaCl/NaHCO3/(NH4)2CO3/water (1:1:1:1) (×3), water, and then dried over sodium sulfate (Na2SO4). The crude product was purified using a SAX column to provide to give the desired (R)-3-(1H-Indol-3-yl)-2-(5-p-tolylethynyl-thiophene-2-sulfonylamino)-propionic acid 5 (0.036 g, 55%).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08530453B2 |
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| 출처 데이터셋 | uspto-grants-2013_09 |
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| ORD ID | ord-712257b6ac254d2f954edd1294596708 |
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| 출처 메모 | uspto-grants-2013_09 |
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