Triethylamine → HCID 58100142, 화합물

HRID 1696849노트

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HRID 1696849 반응식
C(N(CC)CC)C.I[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:11][CH:10]=1.[CH2:30]([O:37][C:38](=[O:44])[NH:39][CH2:40][CH2:41][C:42]#[CH:43])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:30]([O:37][C:38](=[O:44])[NH:39][CH2:40][CH2:41][C:42]#[C:43][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:11][CH:10]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 21185506HCID 21185506, 화합물HCID 58100104HCID 58100104, 화합물

생성물 1

HCID 58100142HCID 58100142, 화합물수율 72.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution containing triethylamine (100 mL), copper (I) iodide (0.50 g, 2.60 mmol) and 57 (7.00 g, 17.40 mmol) dissolved in anhydrous tetrahydrofuran (100 mL) was stirred at room temperature. The reaction flask was vacuumed and then purged with nitrogen three times. The solution was treated with bis(triphenylphosphine) palladium(II) dichloride (1.20 g, 1.70 mmol) and continued to stir at room temperature for 30 min. The reaction mixture was then treated with but-3-ynylcarbamic acid benzyl ester (4.25 g, 20.90 mmol). The reaction was allowed to stir at room temperature for 16 h. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 58 (6.0 g, 72%) as a brown solid: 1H NMR (500 MHz, CD2Cl2) δ 7.85 (dd, 2H), 7.74 (dd, 2H), 7.35-7.32 (m, 5H), 7.27 (d, 2H), 7.22 (d, 2H), 5.08 (s, 2H), 3.93 (t, 2H), 3.39 (t, 2H), 2.81 (t, 2H), 2.62 (t, 2H); m/z (ESI) 477 [C30H24N2O4+H]+.

후처리

  1. custompurged with nitrogen three times
  2. stirringto stir at room temperature for 30 min
  3. stirringto stir at room temperature for 16 h
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resulting residue was purified by column chromatography
  7. washeluting with 0-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-271f262cdb644f5cb02551ecd308eeae
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163758B2

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