Water → Tert-butyl {2-[16-(tert-butyl-dimethylsilanoxy)-hexadecynyl]-4-methoxyp henyl}-carbamate

HRID 969591ノート

反応式

HRID 969591 の反応式
[C:1]([Si:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[CH:24])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].I[C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38].CCN(CC)CC.O>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.CCOC(C)=O>[O:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[Si:5]([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:6])[CH3:7]

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 819182Tert-butyl 2-iodo-4-methoxyphenylcarbamateHCID 23073442Tert-butyl-hexadecane-15-ynyloxy-dimethylsilane

生成物 1

HCID 59017560Tert-butyl {2-[16-(tert-butyl-dimethylsilanoxy)-hexadecynyl]-4-methoxyp henyl}-carbamate収率 92%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of tert-butyl-hexadecane-15-ynyloxy-dimethylsilane (757 mg, 2.15 mmol, 1.5 eq), tert-butyl (2-iodo-4-methoxyphenyl)carbamate (500 mg, 1.43 mmol, 1 eq), [Pd(PPh3)2Cl2] (45 mg, 0.064 mmol, 0.05 eq), CuI (12 mg, 0.064 mmol, 0.05 eq), and Et3N(5 mL) was refluxed for 24 hours. Water (50 mL) and AcOEt (60 mL) were added to the reaction mixture, and the solution was filtered through celite. The filtrate was extracted three times with AcOEt (100 mL). The extract was washed with aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting concentrate was subjected to silica gel flush chromatography (eluate: hexane-AcOEt=98-2) to obtain pale yellow liquid of the title compound (754 mg, yield 92%).

後処理

  1. temperaturewas refluxed for 24 hours
  2. filtrationthe solution was filtered through celite
  3. extractionThe filtrate was extracted three times with AcOEt (100 mL)
  4. washThe extract was washed with aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe resulting concentrate
  8. customflush chromatography (eluate: hexane-AcOEt=98-2)

出典と根拠

ORDレコード
ord-8d0e7573b79f42bf91cb9afbb7bcc4a9
出典データセット
uspto-grants-2007_12
特許番号
US07307098B2

反応ノート

読み込み中…