Triethylamine → HCID 58100142、化合物

HRID 1696849ノート

反応式

HRID 1696849 の反応式
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

参加物

7

反応物 3

HCID 8471TriethylamineHCID 21185506HCID 21185506、化合物HCID 58100104HCID 58100104、化合物

生成物 1

HCID 58100142HCID 58100142、化合物収率 72.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-271f262cdb644f5cb02551ecd308eeae
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

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